Weather in Chicago in October

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Chicago in October October is a wonderful time to enjoy Chicago. With the peek tourist season having past with the summer months, you can enjoy the beautiful fall streets with the locals. Pleasant weather allows you to participate in the full calendar of festive events. While some of the summer traditions have ended, this month is still full of festivals, parades, and other Chicago classics.

As you prepare for your trip to Chicago this fall, keep a few things in mind

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Guide to Chicago Speakeasies

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Though the Prohibition Era is thankfully long gone, Chicago remains fascinated by the idea of speakeasies. There are many around the city that can be found through hidden doors, in back alleys, and behind murals.  These now legal drinking establishments will bring you back in time and remain some of the best kept secrets in Chicago. Read through this guide to find the best speakeasy in a neighborhood near you!

History of Chicago Speakeasies

River North Speakeasies

West Loop Speakeasies

History of Speakeasies in Chicago

In 1920, the United States passed the 18th Amendment, the Volstead Act, more commonly known as Prohibition.  With the passing of this Act, the production, transportation, and sale of alcoholic beverages was now illegal.  This new law, meant to make the United States more moral, only generated further criminal gang activity and corruption.  This also led to the invention of speakeasies, illegal drinking establishments.  

Also referred to as a blind pig or blind tiger, the root of the name comes from the fact that you need to speak easy, or quietly, in public about such places, and while inside the establishment, to not broadcast such illegal activity to the cops and neighbors.

During the 13 years of prohibition, speakeasies popped up across the country.  It is believed that for every legal bar pre-prohibition, 6 speakeasies materialized in its place during prohibition.  These were found in basements, warehouses, and hidden behind store fronts.  The easy money made speakeasies popular to start, and worth the risk. Owners and bartenders were often part of a gang, or conspiring with the gangs, to smuggle in the booze, and pay off the cops if need be.

Chicago is a city that is infamous for the gangs of the 20’s and speakeasies that erupted  across the city.  With gangsters such as Al Capone and Bugs Moran running the streets, it is no wonder why. But with the repeal of Prohibition in 1933, speakeasies were no longer necessary.  However, they are still living on in Chicago culture.

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What to do in Chicago in August

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As the summer months roll on, you will want to be prepared to take full advantage of August in Chicago!  The festivals, concerts, and endless summer fun continues for another summer month in the Windy City. As you prepare for your Chicago adventure, be sure to keep a few things in mind!

Chicago Weather in August

Summer weather continues throughout the city during the month of August. But as the summer starts to wind down, so do the temperatures. The weather begins to cool, and by the end of the month temperatures are a couple of degrees cooler than where they started.

Historically, August remains one of the hottest months, while also maintain the title of wettest month of the year, bringing in 4.9 inches (124 mm) of rain over the course of about 10 rainy days.  Thunderstorms are also common in August, with about 6 stormy days.

Often the thermometer will reach over 70 °F (21 °C) in Chicago, with an average high of 82 °F (28 °C) and low of 63 °F (17 °C). The city averages 4 days this month when the thermometer reaches into the 90s °F (over 32 °C).

The sun shines for an average of 13 hours and 48 minutes a day, with about 9 clear days throughout the month. The average humidity during August is 71%, with the mornings reaching up to 85% humidity, and letting up throughout the day to around 55%.

What to wear/pack for Chicago in August

August is another month for summer temperatures and wardrobes!  Be sure to pack comfortable, light-weight clothing, as well as warmer layers for the cooler evening hours.  As the rainiest month of the year, water resistant shoes, rain jackets, and umbrellas are a necessary addition. Sunglasses and sunscreen are also helpful for many clear days.  This is another great month to take advantage of our miles of coastline, so be sure to throw in a swimsuit as well.


With a packed summer calendar, hotel prices are sure to reflect that Chicago is the place to be. To make your money stretch the furthest, be sure to plan ahead and book hotels as far out as possible.  Even consider staying in one of the newer hotels in the city, as their prices are generally more reasonable and their costumer service reflects their desire to impress and build credibility to match their existing competition.  While there are many attractions downtown drawing guests in, neighborhood hotels are a great option to see a unique part of the city, and save some cash.  Airbnb and hostels are great and affordable lodging choices, and often allow guests to stay in neighborhoods they would not have otherwise experienced.  Neighborhoods are full of Chicago traditions, hosting their own festivals throughout the summer.  Chicago’s public transportation and ride share options allow guests to stay in other parts of the city while maintaining an easy commute to downtown.

August Specific Events

August continues many summer classics in Chicago, while also providing unique and traditional events and festivals.  Find a complete calendar for August in Chicago here.

Some of the city’s most popular August festivals and events include:

Bear’s Training Camp

Olivet Nazarene University: 1 University Ave, Bourbonnais, IL 60914

August 2-13th

Come cheer on the Chicago Bears as they practice and prepare for the season to come!  Most practices are open to the public, and include themed days throughout.  Gates will open at 10:00 am, and practice goes from 11:15 am-1:25 pm.  Don’t forget to sign up for your free ticket here before entering the gates!

Meijer Chicago Bears Family Fest

Solider Field

August 5th, 11:00am

Tickets: $8

Speaking of Da Bears, join the team for this festival at Solider Field!  Outdoor activities begin at 11:00am, followed by a full afternoon with a team introduction, team practice and scrimmage, and concluded with a kid’s run.


Grant Park

August 3-6

The city’s largest music festival returns for another year, and promises to be quite the show with headliners such as Chance the Rapper, Muse, and the Killers. Attracting guests from all over, this Chicago tradition includes hours of live music, from hip hop to heavy metal, as well as comedy and craft booths.  Set between Lake Michigan and the skyline, this is the perfect venue to take in the more than 100 bands with hundreds of thousands of your closest friends during this four day festival.

Lincoln Park Zoo: Adults Night Out

Lincoln Park Zoo: 2001 N Clark St

August 10th, 6:30-10pm

Tickets: $15 ($12 for Lincoln Park Zoo members)

$20 at the door if tickets remain

Enjoy this night out, away from the kids, as you can visit the animals after hours!  Explore the zoo with animal chats, live entertainment, and cash bars scattered throughout. Must be 18+ to attend.

Chicago Hot Dog Fest

Lincoln Park: 1701 N. Stockton Dr.

August 11-13, 11:00am-9:00pm

The Chicago History Museum brings back this new tradition that honors this classic dish that has been a staple in the Chicago diet for the past 100 years.  Serving over 35,000 hot dogs from over a dozen vendors with a unique twist, this is sure to delight the many taste buds at the largest Hot Dog festival in the world.

Bud Billiken Parade

Bronzeville (Martin Luther King Dr. from 39th to 55th)

August 12, 10:00am

This parade has been marching through the streets of the Bronzeville neighborhood since 1929.  This is the largest and oldest African American parade in the world, and concludes with a picnic with local vendors and performers in Washington Park. The focus of this parade is to celebrate children, and prepare for the school year ahead.  Chance the Rapper will be the Grand Marshall this year, as he leads the parade down Martin Luther King Drive.


Broadway in Chicago Summer Concert

Millennium Park: Jay Pritzker Pavilion

August 14, 6:15-7:45

For the 6th summer, guests can enjoy the sounds of current and upcoming Broadway shows performed by cast members, while surrounded by the city lights.  This year’s concert is sponsored by ABC 7 and hosted by Janet Davies.  The music is selected from 10 shows, including Aladdin, Les Misérables, Motown the Musical, and Wicked.

North Avenue Beach

August 19-20, 10:00am-3:00pm

Be prepared to look up for the city’s second most popular festival, which has been a Chicago tradition since 1959! Join millions of other fans that line the Chicago shoreline to watch daredevil pilots, jets, and flying teams that perform for the crowds below. Beyond the U.S. Navy Blue Angels and U.S. Army Parachute Team Golden Knights, you will find water-skiers and boat jumping. Featuring civilian and military pilots, this is the largest show of it’s kind in the country.

Logan Square Food Truck Social

Humboldt Boulevard (from Armitage Avenue to Bloomingdale Avenue)

August 25-27

This festival returns for a second year, providing the city with some of the best local food classics by 20 different trucks.  These mobile delights are accompanied by beer and live music.  Guests can purchase sample tickets to try a little of everything, or order full meals from these Chicago classic trucks.


Chicago Jazz Festival

Chicago Cultural Center (78 E. Washington St.); Millenium Park (201 E. Randolph St.)

August 31-Sept. 3

Celebrate the end of summer with this annual festival!  Started in 1979, this tradition celebrates the diversity and creativity in jazz music, and the talent of local, national, and international artists.  This festival also strives to educate the jazz audience.




Top 10 Rooftop Bars in Chicago

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Summer is a great time to soak in the sun and the expansive views from the rooftop bars dotted across the city!  Below you will find some of our favorite rooftop bars, with the best views of the city, and some of the more creative drinks.  Check out these rooftops, and the scenery that accompanies them!



The Loop; 12 S. Michigan Ave.

Topping off the historic Chicago Athletic Association at 13 stories high is this rooftop bar and restaurant, providing a breathtaking scene of Millennium Park and Lake Michigan.  As one of the best rooftops in the Loop, Cindy’s cocktails are balanced and aesthetically pleasing, to match the view.  The glassed in deck area allows this to be a great decision, no matter the weather!

Hundreds of guests have complimented Cindy’s on Yelp and TripAdvisor, assuring that the drink prices are worth the view!  One Yelper commented, “Cindy’s is highly recommended for anyone visiting Chicago! It is a beautiful space, which includes an open-air terrace that provides a great view of Millennium Park as well as the Lake.”  Another guest commented, “Do you want an amazing view of the Millennium Park? Then you’re at the right place. You get a beautiful aerial view of the Millennium Park! Yes, the line is pretty annoying but definitely worth the wait.”



Reggies’ Trainwreck Rooftop Deck Bar

The South Loop; 2109 S. State St.

Reggies’ is a music lover’s favorite.  This space has been transformed from a run down repair shop, to the music venue, record shop, and bar that is it today! Beyond the good food you will find a rooftop playground, complete with picnic tables, a pool table, and a basketball hoop! This spot is a refreshing change of pace from the downtown rooftops.

Many satisfied customers have reviewed Reggies’ on Yelp and TripAdvisor, calling it, “Just awesome.”  One yelp review stated, “Super chill, South Loop bar. You’ll probably see the most diverse group of people at Reggie’s which makes it even more cool. The rooftop is a good spot to hang out on a nice day.”  Another TripAdvisor review complimented the rooftop deck, “The rooftop bar is one great hang out. Great, relaxed bar scene with fire pit, pool tables, and mere feet from the ‘L’.”


LH Rooftop

The Loop; 85 E Wacker Dr.

Make your way to the top of the London House Hotel to find the sweeping views from this tri-level rooftop. Overlooking the Chicago River, Magnificent Mile, and the famous architecture along the way, this is one of the best angles to take in the surrounding city.

As a more recent addition to the city, this rooftop has already made an impression on many guests.  A yelper stated, “I have been to London House twice, the rooftop, and the city views are amazing you can definitely see Chicago’s architecture. This is a good place to relax, drink and have a good conversation with your pals.”  Another TripAdvisor review also complimented the view, “The rooftop bar is fantastic, with glorious views of the river and downtown Chicago.”



The Loop; 203 N. Wabash

26 stories up, the Virgin Hotel’s rooftop bar, Cerise, hosts a birds eye view of the expansive skyline.  With crafty cocktails and comfy furniture, this is a great spot to begin or end the night. Enjoy the music and lights as you take in the fresh air from balcony that surrounds three sides of this historic building.

Many guests have advertised their positive experience at this bar on Yelp and TripAdvisor. The ambiance and drinks have been complimented, with comments stating, “Really cool atmosphere with amazing rooftop views overlooking downtown. Drinks were about  $10+ for cocktails & $7+ for beers. I’d definitely return… Perfect for a summer night out.” Another satisfied guest stated, “Once you’re up there, awesome ambiance & music accompanied with a swanky interior.”  Others also enjoyed the drinks and rotating music and DJ’s.  “Drinks are on point…some pricey, some reasonable… music was great when we went.”



The Gold Coast; 201 E. Delaware Pl.  

This rooftop sits a block off of the Magnificent Mile in the Gold Coast neighborhood. With a focus on crafty cocktails and quality liquor, this rooftop serves as an oasis on top of the Raffaello Hotel to enjoy some quality conversation and the beautiful scenery.

Many positive reviews prove Drumbar to be a rooftop you won’t want to miss.  One Yelper appreciated this urban escape, stating, “This bar definitely has a local feel too it, since it’s tucked behind the Hancock and right off of Michigan. In my opinion, it’s a bit of a hidden treasure. The drinks are amazing and the ambiance is great.”  Another TripAdvisor guest appreciated the drink menu and atmosphere, “This is a Fantastic space, with great drinks…..a true must do, rooftop bar in Chicago. They have many original drinks, and it’s set up with seating areas so you can have great conversations with your friends.”


The J. Parker

Lincoln Park; 1816 N. Clark St.

Panoramic views of Lincoln Park and the lake are found at The J. Parker, on top of the Hotel Lincoln.  This year-round rooftop bar hosts themed drinks and small plates perfect for every season. With comfy seating and high top tables, this place is perfect for any occasion, and the needed diversion from the heart of downtown.

Many guests have claimed this as their favorite rooftop bar in the city! This bar provides beautiful views of the city, as one Yelper stated, “The view is impeccable! Seriously it is so beautiful I couldn’t stop looking at it.”  Join in the crowd, as one guest recommends; “I have been here a few times and usually this place was more packed than I would like it to be, but that’s only because it’s so great and everybody wants to squeeze in! I will advice you not to hesitate and just join the pack…Whether you are in Chicago on a trip or you are local, you can’t skip visiting this place if you want to enjoy great view of stunning Lake Michigan, cool music and overall great atmosphere!”



River North; 118 W Grand Ave

Taste the color and flavor of Peruvian culture at the rooftop at Tanta.  With Peruvian celebrity chef Gastón Acurio calling the shots, this spot has delicious food and cocktails.  The rooftop deck provides space to enjoy the summer weather while you sip on a pisco sour and enjoy the delectable food.

This restaurant is becoming a River North staple, as seen with the hundreds of positive reviews posted on Yelp and TripAdvisor.  One satisfied Yelper simply stated, “Tanta has a really cool rooftop, beautiful people, and amazing food & drinks.  This is a great place to enjoy the short lived Chicago summer.”  Another positive comment found on TripAdvisor reported, “Tanta is absolutely delicious. The ceviche is phenomenal and the ambiance is blissful. Went there for lunch and sat on the roof. enjoyed the beautiful weather while eating delicious, colorful, and flavorful food.”


Up & Up

Wicker Park; 1600 N. Milwaukee Ave.

This rooftop lounge above the Robery Hotel showcases the beauty of the city.  Hovering above the ‘L’ tracks, you will find views of the skyline in the distance and the dynamic neighborhood that surrounds this hotel. Enjoy your inventive cocktail with the sun and the view.

As one of the newer rooftops in Chicago, this bar has already started to receive positive feedback from customers. Customers enjoy this rooftop escape in the vibrant Wicker Park neighborhood, as one Yelper commented, “Hands down the best view in Wicker park.” Another review stated, “5-star for the beautiful skyscraper view of Chicago. This place is right next to the Damen blue station which is a huge plus.”


IO Roofscape

River North; 127 W Huron St.

Nestled in River North, you will discover IO Roofscape within the Godfrey Hotel.  With a spacious lounge and modern vibe, this rooftop provides indoor and outdoor seating for every season, and every time of day.  This urban, upscale rooftop serves chef crafted cocktails accompanied with a view.

This has been a popular spot for years, as customers have commented on everything from the atmosphere to the food.  One yelp review stated, “The outdoor seating is great! They have cabanas, comfy lounge seating, tables for dining, etc. I also like their inside lounge seating. It’s classy with dim light setting.”  Many locals have used this as a platform to show off their city, as one TripAdvisor review stated, “It’s my go-to bar for visitors. Great view…Great service and drinks”



Streetersville; 259 E Erie St.

Tucked away in the midst of the Medical District, you will discover this rooftop escape.  With stunning views of the surrounding buildings, you will find the perfect location for an innovative cocktail inspired by an Irish American flavor, as well as a seasonal small plates or a full course meal.

Hundreds of reviews have showed that this is another rooftop you will want to add to your list.  One Yelper complimented the food, drinks, and atmosphere, stating, “The ambiance is beautiful, really elegant and the terrace is to die for. They have really cool cocktails and great food.”  Another positive review said, “My new favorite Chicago restaurant, hands down! Beautiful outdoor seating area and the wait was not bad! Not overly crowded or loud but great energy. Food presentation was perfect, and delish!”

Free Chicago Tourist Attractions

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Navy Pier

600 E. Grand Avenue

Navy Pier remains one for the Midwest’s top tourist attractions, bringing in 8 million guests annually. Take a stroll down to boardwalk to catch a sweeping view of the Chicago skyline. During the summer months, Navy Pier provides free fireworks Wednesday and Saturday nights from Memorial Day to Labor Day. Navy Pier jets out into Lake Michigan, providing entertainment for the whole family with shops, restaurants, and amusements rides such as the Ferris Wheel and carousel. Along the pier you will also find the Children’s Museum, Chicago Shakespeare Theater, and boat tours, all at an additional cost. Plus, the view of the Skyline from Navy Pier is amazing!  Check out our self-guided tour of Navy Pier.


Lincoln Park Zoo

2001 N. Clark Street

Founded in 1868, the Lincoln Park Zoo is the oldest free public zoo in the country. It is not only known for its vast array of animals on display but also for its beautifully landscaped gardens, wide walking paths, and plenty of shade trees interspersed throughout. This is definitely a warm and inviting atmosphere to spend a vacation enjoying and learning everything you could about all of nature’s wildlife that surrounds us.  Check out our blog about visiting Lincoln Park Zoo.


Harold Washington Library Center 

400 S. State Street

The Harold Washington Library is one of the largest libraries in the United States.  The post-modern style building with approximately

756,000 square feet hosts rotating art exhibits, a permanent art exhibit, free classes and workshops, events, pianos in practice rooms on the music floor, free Wi-Fi and a rooftop garden.  Our very own Birth of a Skyscraper: Chicago Architecture tour features this building. Mon-Thurs: 9am-9pm; Fri-Sat: 9am-5pm; Sun: 1pm-5pm



Lincoln Park Conservatory

2391 N. Stockton Dr.

Escape the city air as you step into the Lincoln Park conservatory. Also free to the public, this conservatory and botanical gardens contains four rooms as a serene escape from the Chicago climate, stocked with tropical and exotic plants from around the world.  Park Hours: 9:00 AM-5:00 PM


City Gallery at the Historic Water Tower 

The Water Tower and pumping station are among the few buildings that survived the Chicago Fire of 1871.  Built in 1869 with limestone, this neo-gothic building resembles a little castle nestled in the heart of the Magnificent Mile. Currently, it houses a city art gallery which displays the work of local photographers and artists.  It is definitely worth a peek! The address is 806 N. Michigan Ave. Mon-Fri: 10am-6:30pm; Holidays, 10am-4pm.


Chicago Riverwalk

Enjoy a stroll along the Chicago River with the backdrop of fantastic architecture and the promise of a tasty snack!  The Chicago Riverwalk has restaurants, wine bars, and many delicious places to spend an afternoon.  If you prefer a guided tour, hop onto our Riverwalk & History tour!


Buckingham Fountain

301 S. Columbus Dr.
Grant Park is one of the oldest parks in Chicago dating back to 1835.  The large green space makes it a perfect place to hold events like the Chicago marathon and the Taste of Chicago, which is an annual Chicago festival.  The centerpiece of the park is one of the largest fountains in the world.  Buckingham Fountain, a rococo-style fountain, was given to Chicago as a gift in 1927.  The fountain was manually operated until 1980.  From 10am-11pm- there is a water display on the hour for about 20 minutes!


Chicago bike tour Buckingham Fountain

What to Do In Chicago In July

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Summers in Chicago are truly the most wonderful time of the year as the city escapes hibernation and surpasses spring showers. These warmer months usher in a full calendar of Chicago festivals, events, and traditions. July is one of the best months to soak in the sun and Chicago culture. As you prepare for your adventure, be sure to keep a few things in mind!

Chicago Weather in July

Chicago is a city with all four seasons, and if you are lucky, you can experience all for of these seasons during your short stay. With that in mind, historically speaking July in Chicago tends to be hottest month of the year, and is one of least windy months here in the Windy City, providing minimal relief during our hottest hours. Average temperatures in Chicago reach as high as 81-87 degrees Fahrenheit (27-31 C) and settle for an average low of 61-66 degrees Fahrenheit (16-19 C). On average, a few days out of the month, temperatures will peak over 90 degrees Fahrenheit (32 C).

The sun shines for 14-15 hours a day, with minimal cloud cover and an average rain accumulation of 3-4 inches (7-10 cm) spread throughout the month. The average humidity during July is 68%, with the mornings providing more humidity.

What to wear in Chicago in July

Pack for the summer weather! With July being the hottest month, you will want to be prepared with comfortable, light weight clothing.  Sweatshirts or light jackets may come in use during the evening hours. Comfortable walking shoes are also essential for your visit to Chicago. Don’t forget your swimsuit and sunscreen so you can take advantage of our beaches!


July Specific Events

The month of July provides the city with various events and over 20 festivals, covering different neighborhoods, themes, cultures, and music genres.  Find a complete guide to Chicago’s July calendar here.

Windy City RibFest in Uptown

4800 N. Broadway St.

June 30- July 2

Explore the historic neighborhood of Uptown while local and national ribbers work to impress you with their saucy slabs of meat. This festival also includes eclectic music performances, arts, crafts, and family friendly events!

Lion’s Club International Convention Parade

State St. from Lake St. to Van Buren

July 1, Parade starts at 9am

This year, Lion’s Club international is turning 100! Each year, this organization hosts a convention with a parade on the second day.  This festive event hosts Lions representing over 130 countries, and often in traditional colors and attire.  Participants will hold their countries flag with pride and many can be found singing and dancing along the route. This has been a tradition since the 1920’s.

Fourth of July Festivities

Celebrate the 4th of July in Chicago as the city honors this country with a day full of American classics, including baseball, concerts, and fireworks.

Both of the city’s baseball teams host games on this holiday.  The Chicago Cubs take on the Tampa Bay Rays at Wrigley Field, and you will find the Chicago White Sox going up against the Oakland Athletics at Guaranteed Rate Field.

The annual tradition of a holiday concert continues as a part of the Grant Park Music Festival with Independence Day Salute, held in Jay Pritzker Pavilion in Millennium Park starting at 6:30.  After the concert you can catch one of Navy Pier’s best firework displays of the summer, with patriotic music in the background.  For a better view of the fireworks and the city as a whole, consider buying tickets ($39) for the Freedom Fest 2017 at Navy Pier, complete with BBQ, a DJ, and dancing.

Taste of Chicago

Grant Park: Jackson and Columbus

July 5-9

Join in the fun by attending the world’s largest food festival! Sample your way through Chicago’s food scene as you enjoy music and family friendly activities during this 5 day festival. A Chicago tradition since 1980, this isn't one you will want to miss!

Pitchfork Music Festival

Union Park: 1501 W. Randolph Street

July 14-16

With over 40 bands performing for crowds of 50,000 people during this three day festival, Pitchfork Music Festival promises to be an energizing event showcasing the best in new and rising music as it returns for the 12th year. Beyond the music, this festival hosts local vendors, supporting Chicago's arts and food culture.

Taste of River North

Ward Park: N. Kingsbury and W. Erie

July 21-23

For the 16th year, this festival will draw in crowds to experience one of Chicago’s most entertaining destination neighborhoods. Nestled in between the Chicago River and the glowing skyline, this festival highlights some of the best of River North, with dynamic chefs and restaurants providing the food, and local bands adding non stop music. Local vendors and family friendly activities enrich the festivities.

CrossTown Classic

July 24-27

Each year, Chicago’s two baseball teams, geographic rivals, match up in a four game mini series. Cheer on the Cubs, White Sox, or both, as these hometown teams face off once again.

Wicker Park Fest

Milwaukee Ave., from North Ave. to Paulina St

July 29-30

Called out as “Chicago’s Best Street Festival of the Summer” by the Chicago Tribune, this tradition continues to draw in crowds from across the city and country. This festival highlights the personality and culture of this neighborhood, with a prosperous music history, vintage shops, dynamic nightlife, and delectable restaurant scene. With over 40 bands performing during this three day festival, in addition to the arts and craft tents, this event is sure to leave you more than entertained.


Throughout the summer season, you will find many other Chicago summer traditions to occupy your time, such as free movies in the park, exercise classes, and some of the best farmers markets.  Check out our 10 Free Things to do in Chicago this Summer blog.


With summer festivals and activities in full swing, hotel prices reflect that everyone wants to be in Chicago! With the increase in trends such as Airbnb, hotel demand downtown has seen a decline in the past year. In the year 2017 the downtown area will have completed 7 new hotels, adding over 2,000 new rooms! While this extra supply could benefit those hoping to make a visit to Chicago, do be aware that historically the hotel demand and prices rise druring these summer months.

To save money during these peak weeks, be sure to plan ahead an book hotels as far out as possible, as their prices reflect the current demand. Many guests aim to stay in the heart of downtown to be near the summer festivals in Grant Park. Consider staying in a hotel in a neighborhood to experience the character outside of downtown, and to find better price tag. If you are willing to be adventurous and try a newer hotel you will find better rates, as the hotel does not yet have the credibility to charge as much as a more established hotel, and they will work harder to impress you.

Airbnb and hostels are great lodging choices, and often allow guests to stay in neighborhoods they would not have otherwise experienced. Chicago’s public transportation and ride share options allow guests to stay in other parts of the city while maintaining an easy commute to downtown.

Chicago’s Beautiful Parks

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Millennium Park

201 E. Randolph

Chicago bike tour BeanMillennium Park was revealed in 2004 and quickly became one of Chicago’s favorite parks.  Constructed within the borders of Grant Park, this park provides a diverse event calendar with free entertainment year round. From concerts to exercise classes to festivals, this park pleases millions of locals and tourists each year. Check out our self-guided tour of the park!

Jay Pritzker Pavilion: With a capacity of 11,000, this pavilion has become the centerpiece of Millennium Park. With an advanced sound system and designed for its acoustics, the Jay Pritzker Pavilion hosts many musical events and festivals.

Cloud Gate: More commonly known as the bean, this piece of art design by Anish Kapoor was revealed to the public in 2005. Created with 200 stainless steel plates, this piece of art has become one of Chicago’s most distinguishing landmarks

Crown Fountain: This interactive sculpture is a family favorite in the heat of the summer. Standing at 50 feet (15 m) tall, this fountain has two towers featuring videos of 1,000 Chicago residents’ faces. Every seven minutes, the faces pucker their lips and spray buckets of water out of their mouths onto a swarm of eagerly awaiting kids.

Boeing Galleries: On the north and south end of Millennium Park you will find the Boeing Galleries. These outdoor galleries display rotating contemporary art instillation’s by living nation and international artists.

Chicago Bike tour Crown FountainLurie Gardens: This five acre perennial garden holds native and foreign plants throughout every season. This serene escape is designed to symbolize Chicago’s transformation from a marshland to the city that it is today. The garden is protected by a 15 foot tall hedge, meant to illustrate Carl Sandburg’s description of Chicago, the “City of big shoulders”.

Seasonally: Be sure to check the calendar for current events in Millennium Park! In the winter it is home to the McCormick Tribune Ice Rink, which is free to skate but offers $12 skate rentals. During the summer months, there are free daily events, including movies in the park, concerts, exercise classes, and many festivals in between! Check out our Top 10 Free Things to do this Summer.


Grant Park

337 E. Randolph Street

Chicago bike tour Buckingham FountainNicknamed Chicago’s “front yard,” Grant park is one of Chicago’s oldest park, and has continued to expand over time. Some of the features of this park include world class museums (Shedd Aquarium, Adler Planetarium, the Art institute, and the Field Museum of Natural History), harbors, artwork, Buckingham Fountain, as well as Millennium Park and Maggie Daley Park.

Grant Park also hosts annual events such as The Taste of Chicago, Lollapalooza, and contains the start and finish lines of the Chicago Marathon.

Spirit of Music Garden: This 4,900-square-foot open space hosts different events throughout the year. One of the more popular events is Summer dance, hosted during the summer months as 43 different live bands perform and guests show off their best dance moves. Show up a little early for a free dance lesson!

Buckingham Fountain: Gifted to the city in 1927, this is one of the world’s largest fountains. From April until October, this fountain runs from 8:00AM to 11:00PM, shooting water 150 feet into the air for 20 minutes every hour. At night, this fountain is illuminated with different colors.


Maggie Daley Park

337 E. Randolph St.

Maggie Daley Park is the newest addition to Grant Park, located in the northeast corner. These 20 acres of transformed space have provided a great play space for kids, and is a park prepared to entertain in every season.

Skating Ribbon: The Skating ribbon provides a unique skating experience, with inclines and declines in the ice as guests loop a quarter mile (0.40 km) around the rock wall. Skating is free, with the option for $12 skate rentals. During the warmer months, the ribbon serves as a walking path and a perfect space for kids to scooter around with the skyline serving as the perfect backdrop.

Play Garden: This kid-friendly park houses six different playgrounds for children 12 and under across 3 acres. Each playground has a creative theme and is designed for a different age group.

Tennis Courts: The tennis courts are open from April to November, and are free of charge for walk ups. Guests can also reserve a court for $15 Monday-Friday from 7:00AM- 5:00PM, and for $20 Monday-Friday, 5:00 PM – 9:00PM and during the weekends.


Lincoln Park

500-5700 N. Lake Shore Drive Irving Park and Recreation Drive

This land marks the initial cemetery for the City of Chicago, but has been transformed into the year round favorite that it is today. This park hosts more than just green grass. Lincoln Park is lined with beaches along Lake Michigan, full of sports fields, and home to the Lincoln Park Zoo and Conservatory.  Most importantly- you will find important monuments and statues, including “Lincoln the Man” a masterpiece realized by Augustus Saint Gaudens.  You will find a bronze of the French explorer LaSalle, who predicted that one day a great city would rise here!  You will see a temperance fountain and relic from the 1893 World’s Colombian Exposition, originally named for temperance leader Francis Willard. All this history is quietly suggested by the enduring bronze forms which reside along the lakefront, surrounded by a landscape of lawns and trails, gardens and ponds.

Garfield Park

100 N. Central Park Ave.

This 40 acres of land located west of downtown includes flower gardens, a lagoon, and the Golden Dome field house used for recreational activities. The most notable feature is the Garfield Park Conservatory, one of the largest conservatories in the country located at 300 N. Central Park Ave. The Conservatory is considered a “landscape art under glass” houses thousands of plants throughout its eight rooms. Highlights include diverse tropical plants, 84 variations of a palm trees, and an assortment of cacti.

Jackson Park

6401 S. Stony Island Ave.

This park was designed by landscape architects Frederick Law Olmsted and Calvert Vaux for the purpose of being the site of the 1893 World’s Fair. The Museum of Science and Industry is the only building remaining from the fair, but this beautiful landscape also houses the stunning Osaka Japans Garden on Wooded Island.


Free Things to do in Chicago

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Boxing Bear Street Art (Free to see!)The Free Chicago Riverwalk A Sunny Chicago Skyline (Free View!)Smiling African American Man on Crown Fountain (A Free Park)

Free Things To Do In Chicago

Experience the Windy City in all its glory without breaking the bank. Check out this list of free things to do in Chicago. Chicago provides free and affordable activities to entertain locals and tourists all year long! Between the museums, parks, and festivals, kids and adults alike will have more than enough to keep them amused and their pockets full.  Be sure to check out our partner, Choose Chicago for amazing suggestions as well. Did we miss something?  Let us know and we will add it to our list!

For more great ways to save on your visit to Chicago, read about the various discount passes.