For those of you who don’t know, Chicago is my birthplace—the Windy City. Everybody I meet while traveling gets the same advice from me: “Come to Chicago in the summer, between June and the first two weeks of September. It’s one of the best cities in the world for three and a half months.”
And I’m not the only one who thinks Chicago is an incredible city. Readers of Condé Nast Traveler have voted Chicago the Best Big City in the United States for 10 consecutive years, from 2017 through 2026, as part of the magazine’s annual Readers’ Choice Awards.
Summertime Chicago has so much to offer, partly because the weather isn’t as much of a deterrent during this season. Moreover, the locals are happier and more enthusiastic, which translates into better energy throughout the city. It’s nice to be somewhere where the people who live there are in a good mood.
There are a million things to do here, but I’ve narrowed them down to 14. I’ll also try not to list all the obvious attractions you might find in other blogs or articles, like the Sky Deck at Willis Tower or TILT at 360 Chicago. If you don’t see certain major activities, I’ve left them out on purpose.
This is a local’s guide to Chicago! Read it all the way the way through. Without further ado, let’s go!
1. Watch a Chicago Blackhawks Game and See the Michael Jordan Statue
This is an extremely underrated activity for any traveler and is especially exciting for a hockey fan! When the team is having a good season, even better.
For those who don’t know, the Chicago Blackhawks are our professional hockey franchise in the NHL. If you’ve never attended a hockey game at this level, check it out. It’s a memorable experience when seen live and in person.
Chicago has very loyal sports fans and a rich history in hockey, American football, and basketball, so you can expect a passionate crowd.
One of the most unique aspects of attending a Blackhawks game is the singing of the United States national anthem. The atmosphere during the anthem is electric, with fans cheering throughout the performance.
While you’re at the United Center, don’t forget to see the famous Michael Jordan statue, honoring the Chicago Bulls legend who helped bring six NBA championships to the city.
2. Visit a Chicago Street Festival
During the summer months, Chicago hosts a huge variety of street festivals celebrating different cultures, art, food, music, literature, and more.
Typically, two to four blocks of a street are closed to traffic and filled with vendors, food stands, and performance stages. Many festivals take place over the weekend, starting Friday evening and ending Sunday night.
You can find upcoming events on local websites, Choose Chicago, and community social media pages. There’s usually something happening every weekend during the summer.
Not all festivals are equal. Some are crowded and energetic, while others have a more relaxed neighborhood atmosphere. You don’t want to show up somewhere that doesn’t match your vibe. I’ve written a useful guide to festival season in Chicago if you’d like to know more.
There’s something for everyone, from a local neighborhood fairs to the city’s major music festivals.
Don’t miss out!
3. Grab a Coffee and Walk, Bike, or Rollerblade Along the 606
The 606, also known as the Bloomingdale Trail, is an approximately 4.3-kilometer (2.7-mile) elevated park and recreational trail running east–west through several neighborhoods on Chicago’s Northwest Side.
Built along a former railroad line, it sits above street level and offers a different perspective of the surrounding neighborhoods.
The trail is generally open from 6 a.m. to 11 p.m.
I suggest grabbing a coffee or smoothie from a nearby shop in Wicker Park, then entering the 606 near the intersection of Milwaukee Avenue and Leavitt Street.
From there, just relax and enjoy the views. It’s a great place for a casual walk, bike ride, or some rollerblading.
4. Enjoy Stand-Up Comedy, Improv, Theater, or Live Music
Chicago has a historic comedy scene and a rich tradition of live performances. You should take advantage of it while you’re here.
COMEDY AND IMPROV
Some notable venues include Zanies, iO Theater, Laugh Factory, and The Second City.
The Second City is particularly famous, although I don’t personally care for it.
I prefer Zanies because of its intimate setting. It’s a great place to enjoy talented comedians and have a few laughs.
THEATER
For plays and live acting, consider the prestigious Goodman Theatre, one of Chicago’s oldest nonprofit theaters, founded in 1922.
It’s an internationally recognized venue with two performance spaces, known for its variety of productions, including classic dramas, musicals, and world premieres.
The theater also has a strong community focus and offers educational programs and discussions related to its productions.
Another option is one of Chicago’s most recognizable landmarks: The Chicago Theatre.
This iconic venue hosts concerts, comedy shows, family events, theatrical performances, and even live podcast shows.
Even if you don’t plan to attend a performance, consider taking a guided tour to see its magnificent interior and learn about its history.
LIVE MUSIC
For live music, I recommend:
- Subterranean
- Green Mill
- Empty Bottle
- Kingston Mines
- The Hideout
- The Salt Shed
Each venue attracts a different crowd and specializes in different styles of music.
Check them out and see which one suits you. They’re all established Chicago venues, although Kingston Mines is probably the most tourist-oriented of the four.
5. Explore Garfield Park Conservatory
The Garfield Park Conservatory is often described as landscape art under glass. It houses thousands of plants across eight indoor gardens, along with approximately 10 acres of outdoor grounds.
Each indoor space creates a different environment.
- Fern Room: Recreates a prehistoric-looking, swampy landscape with ferns and a lagoon.
- Palm House: Features a tropical setting filled with towering palm trees.
- Desert House: Contains a collection of cacti and other succulents.
- Aroid House: Displays a variety of aroid plants, including species commonly grown as houseplants.
- Show House: Hosts rotating seasonal flower displays.
The conservatory also features special exhibitions and a Children’s Garden designed for educational activities.
It’s a pleasant getaway from the busy city and gives you a reason to explore another part of Chicago.
I recommend taking an Uber or another rideshare service if you want a convenient way to get there.
6. Eat at Jim’s Original and Grab Italian Lemonade at Mario’s
Chicago has no shortage of iconic foods, from its amazing pizzerias to Chicago-style hot dogs and Italian beef sandwiches. But out of all the classics, the Polish sausage, or just “Polish” to sound more local, is my personal favorite.
And Jim’s Original is the godfather.
They prepare a delicious combination of Polish sausage, mustard, sport peppers, and grilled onions.
Located near the University of Illinois Chicago (UIC), Jim’s is conveniently situated close to bars and restaurants around Halsted Street.
About a 10–15-minute walk away, at 1068 W. Taylor Street, you’ll find Mario’s Italian Lemonade.
After finishing your Polish sausage, walk over to Little Italy and grab yourself a refreshing Italian ice.
Usually operating from May through mid-September, Mario’s is a neighborhood staple.
You can conveniently walk through the UIC campus on your way from Jim’s to Mario’s, making this a nice little food excursion.
7. Visit the Art Institute of Chicago and the Griffin Museum of Science and Industry
These are two of the best museums in the city, and I highly recommend visiting both.
GRIFFIN MUSEUM OF SCIENCE AND INDUSTRY
The Griffin Museum of Science and Industry, formerly known simply as the Museum of Science and Industry, is one of the largest science museums in the world.
It’s housed in a historic building originally constructed for the 1893 World’s Columbian Exposition.
The museum has an educational focus, with several engaging and interactive exhibits covering science, technology, engineering, and industry. It’s also home to thousands of fascinating artifacts.
ART INSTITUTE OF CHICAGO
The Art Institute of Chicago is consistently recognized as one of the world’s leading art museums.
Its collection includes famous works of modern and contemporary art, ancient and Asian art, and American and European paintings. With roughly 300,000 works spanning many different mediums, there’s an enormous amount to explore.
Plan to spend plenty of time here if you’re an art enthusiast. I’ve visited some fascinating museums along with this one during my travels, and a few have left a lasting impression on me.
The Art Institute is also conveniently located just a few blocks from Cloud Gate, better known as The Bean, one of Chicago’s most recognizable landmarks.
8. Enjoy the Chicago Skyline From LondonHouse or Kennedy Rooftop
Chicago has some excellent rooftop bars, and these two offer very different perspectives of the city.
LONDONHOUSE — Downtown Chicago
LondonHouse is located downtown along the Chicago River, making it a great place to appreciate the architecture and skyline from above.
Its rooftop offers gorgeous views of the river, bridges, and surrounding skyscrapers.
It’s especially impressive if you’re interested in seeing Chicago’s downtown buildings from a different angle.
KENNEDY ROOFTOP — Wicker Park/Bucktown
Kennedy Rooftop is located in the Wicker Park/Bucktown area, away from the main downtown hotel and tourist district.
That’s what makes it interesting.
Instead of being surrounded by downtown skyscrapers, you get a more distant perspective of the Chicago skyline, with the surrounding neighborhoods in the foreground.
It’s also relatively close to an access point for the 606, making it a convenient stop before or after exploring the elevated trail.
Both rooftops are worth considering, depending on the kind of view and atmosphere you’re looking for.
9. Rent a Bike and Explore Chicago’s Neighborhoods and Lakefront
Chicago is a GREAT city to explore by bicycle.
After covering the Lake Michigan waterfront, I’ll suggest some bike-friendly streets and neighborhoods to explore outside downtown—which you definitely should.
RIDE ALONG LAKE MICHIGAN
Riding along Lake Michigan might make you want to live here.
On one side, you have an enormous lake and beaches. On the other, Lake Shore Drive, parks, and towering apartment buildings.
The best place to ride is the Lakefront Trail, which stretches along Chicago’s shoreline.
Some notable places to explore during your ride include:
- Montrose Beach
- Belmont Harbor
- Chicago Yacht Club
- DuSable Harbor
- Diversey Harbor
There’s a lot to see, and you can easily spend hours riding along the waterfront.
EXPLORE CHICAGO’S NEIGHBORHOODS BY BIKE
Here are some of my favorite streets and areas for cycling beyond downtown.
Milwaukee Avenue — Wicker Park and Logan Square
Ride northwest or southeast along Milwaukee Avenue between Halsted Street and Kimball Avenue.
This stretch crosses the Kennedy Expressway and passes through Wicker Park and Logan Square.
It’s a popular cycling corridor with bike lanes and plenty of shops, restaurants, and neighborhood activity along the way.
Feel free to do your own research or simply explore.
Humboldt Park
Humboldt Park is an enormous green space that’s enjoyable to ride through.
North Avenue and Division Street provide connections to the area, although bike-lane conditions vary along these roads, so plan your route carefully.
And while you’re nearby, grab some Puerto Rican food along Division Street!
Lincoln Avenue — Lincoln Park to Lincoln Square
Take Lincoln Avenue northwest or southeast between Fullerton Avenue and Lawrence Avenue.
You’ll pass through several residential neighborhoods and get a more authentic feel for everyday Chicago life.
Clark Street and Broadway — Lakeview and the North Side
Another option is riding Clark Street between Fullerton Avenue and Irving Park Road, passing through neighborhoods including Lakeview and Wrigleyville.
Alternatively, explore Broadway between Diversey Avenue and Argyle Street, where you’ll pass through Lakeview, Uptown, and the area around Asia on Argyle, known for its many Asian restaurants and businesses.
Each of these routes offers a different experience. Check them out on Google Maps and see which one appeals to you.
One last thing: Chicago’s bike infrastructure varies by street, so pay attention to traffic and use protected bike lanes or quieter streets whenever possible.
10. Explore All of Chicago’s Architecture & Take an Architecture Boat Tour
Chicago is famous for its architecture, and many people consider its skyline among the best in the United States. I have a list of personal recommendations, and we’ll start with the Chicago River architecture boat tour, Ideally enjoyed on a nice, sunny day.
It’s one of the best ways to appreciate the city’s skyscrapers downtown. During the tour, you’ll learn about important events in Chicago’s history, including the Great Chicago Fire of 1871 and the rebuilding that followed.
The guide will share information about architectural styles, famous buildings and architects, and Chicago’s role in developing the modern skyscraper.
The sunlight reflecting off the glass windows of downtown buildings adds something special to the experience, which is why I recommend going on a clear day.
Walking through downtown and looking up at the architecture is one thing, but seeing it from the river gives you a completely different perspective.
MORE ARCHTECTURE WORTH EXPLORING
Hyde Park
A historic and culturally rich neighborhood home, Hyde Park is home to the University of Chicago, the Frederick C. Robie House designed by Frank Lloyd Wright, the Garden of the Phoenix (formerly Osaka Garden), and beautiful historic homes.
Loop and Financial District Interior Architecture Tour
You’ll miss out on a lot if you don’t go INSIDE some of Chicago’s incredible buildings.
The interiors are often just as impressive as the exteriors. I highly recommend taking a guided walking tour focused on downtown architecture and historic interiors.
Here’s an example of an architecture interiors tour on Tripadvisor. If that particular tour is no longer available, you can easily look for another one.
Frank Lloyd Wright Home and Studio Tour
Located in nearby Oak Park, the Frank Lloyd Wright Home and Studio offers a look into the life and work of one of America’s most influential architects.
Wright is known for his approach to organic architecture and his innovative design concepts.
A must-see for anyone interested in architecture and design.
11. Eat the Garrett Mix at Garrett Popcorn Shops
Home of my favorite popcorn.
I’m traditionally pretty strict with my diet, so I don’t eat much of this kind of food anymore. But I can’t deny that Garrett’s popcorn is delicious and ADDICTIVE.
The business dates back to 1949, when its first Chicago shop opened.
Get a taste of Chicago history and be sure to order the famous Garrett Mix, which combines CaramelCrisp and CheeseCorn.
The sweet-and-salty combination is simply delicious!
12. Take a Ride down Lower Wacker Drive
Have you ever seen The Dark Knight?
If you have, I’m sure you remember the scene where the Joker pulls out a bazooka during the downtown chase.
Well, part of that sequence was filmed on Lower Wacker Drive.
If you get a chance, drive through this underground roadway system. It’s like seeing the basement of downtown Chicago.
Wacker Drive has multiple levels, with Upper Wacker at street level and Lower Wacker running underneath it.
There are also lower service and access areas, sometimes referred to as Lower Lower Wacker, used for deliveries, utilities, and other functions.
Lower Wacker serves as an alternative route through parts of downtown, allowing drivers to avoid some of the busy surface streets.
Certain sections have pedestrian access, but much of the roadway is designed for vehicles. If you’re exploring on foot, stick to designated pedestrian areas.
It’s one of Chicago’s more unusual urban features, and definitely worth seeing if you’re interested in the city’s infrastructure or movie locations.
13. Walk Along the Adler Planetarium for an Incredible Skyline View
If you want one of the best views of the entire Chicago skyline, head to the waterfront near Adler Planetarium.
The planetarium sits on Northerly Island, just south of downtown, with an open view of the skyline across the water.
You don’t need to enter the museum to enjoy the scenery.
Walk along the waterfront near the planetarium and take in the buildings rising above Lake Michigan.
GO AT NIGHT!
Seeing the illuminated skyline reflecting off the water is a completely different experience from visiting during the day.
For more viewpoints, check out this guide to Chicago skyline views.
14. Explore Chicago’s Ethnic Neighborhoods: Little India on Devon Avenue & Asia on Argyle
LITTLE INDIA ON DEVON
For something completely different from downtown Chicago, head north to Devon Avenue, home to the city’s well-known Little India district.
This stretch of Devon, particularly around Western Avenue and extending through parts of West Ridge, is lined with Indian and other South Asian restaurants, grocery stores, clothing shops, jewelry stores, and specialty businesses.
You’ll find everything from traditional sweets and spices to colorful clothing and regional dishes.
The neighborhood also reflects Chicago’s broader South Asian community, with businesses and restaurants representing several different cultures. It’s a great place to walk around, explore the shops, and try food you might not find in the more tourist-oriented parts of Chicago.
If you enjoy discovering different cultures through their food and neighborhoods, Little India is definitely worth a visit.
ASIA ON ARGYLE — CHICAGO’S LITTLE SAIGON
Located in Chicago’s Uptown neighborhood, Asia on Argyle is a historic cultural district known for its large Vietnamese community. Also called Little Saigon, the area developed during the 1970s as Chinese entrepreneurs and immigrants and refugees from Vietnam and Cambodia established restaurants, grocery stores, and other businesses.
Today, the streets surrounding the Argyle Red Line station are filled with Vietnamese restaurants serving phở and bánh mì, Chinese eateries offering dim sum, Asian supermarkets, bakeries, and specialty shops.
One of my favorite snacks are the sesame balls with red bean paste from Chiu Quon Bakery. I can’t tell you how many times I’ve grabbed some on the go before jumping on the train right next door!
During the summer, the neighborhood also hosts the popular Argyle Night Market, featuring street food, local vendors, and live entertainment. It’s a great place to explore on foot, try some authentic Asian cuisine, and experience another side of Chicago’s cultural diversity.
