25 Fun Things to do in Chicago this Summer
Disclaimer: We are not paid to promote any restaurant, hotel, activity, product, or attraction. All opinions are subjective and based on our personal experience. Your experience may be different.
The Windy City is one of the best places to be during the summer season (and I am not just saying this as a native!). There are so many events, festivals, and beautiful places to explore, making it the ideal vacation destination for anyone who likes sports, music festivals, and outdoor recreation. Having lived in the city for over 20 years (I grew up on the southside), I have had plenty of fun summertime adventures over the years.
While I am more of a fall/winter person, I have to admit that this city is home to an awesome urban bike path along Lake Michigan, along with some of the best museums in the country. Also, the summertime is the best time to appreciate the best skyline in the country (it ranks number one for me with Pittsburgh being a close second). I’ve traveled all over the country in the last 20 years and I still love coming back home to enjoy all the amenities in this world-class city (there is no place like it).
Whether you are in the mood for fitness, world-class museums, great food, or top notch entertainment, you are bound to find something fun to do. In my guide, I will highlight a range of activities to hopefully inspire everyone to take a trip. While the city has a bad reputation, there is plenty of beauty to be found and a long list of world-class attractions.
1. Walk/bike the Lakefront Trail
I only wish I would have found out about this wonderful urban path sooner. It is a great place to bike or even train for a half marathon due to the lengthy distance. This beautiful trail runs for 18 miles along Lake Michigan. Beautiful scenery, beaches, and plenty of fun stops along the way will keep you more than motivated to finish the entire 36 mile course. I’ve biked a lot of great urban paths during my years traveling and the scenery here is hard to top.
You will notice a lot of active types (runners, bikers, dog walkers) out enjoying the nice weather before the long winter arrives. Overall, it is just such a motivating place with big city views, gorgeous lake scenery, and lots of fun detours along the way.
Some of my favorite stops include: Oak Street Beach, The Field Museum, Lincoln Park Zoo, and the Planetarium for the amazing skyline pictures!
Address: 1600 N Lake Shore Dr.
2. See a Cubs game
Cheering on the Cubs at Wrigley Field is always a fun experience. Many years ago, I remember when we used to be able to walk around the stands and sit wherever we wanted – this was when you could get tickets for like 7 bucks. I remember when I was younger, it was so easy to get baseballs signed after the game. I was a pretty big fan of Ryne Sandberg and was so excited to get my ball signed!
For the most authentic experience, I recommend sitting in the bleachers. Fans are super passionate about all their teams in this city, especially the Cubbies. If you are lucky, you may get to hear fans singing the catchy “Go Cubs Go” song if they win.
Baseball fan or not, I recommend taking this opportunity to visit the second oldest ballpark in the country (next to Fenway!). Did you know that the Chicago Bears used to play at Wrigley Field before they had Soldier Field? On a side note, the post game bar scene in Wrigleyville is entertaining for both Cubs and non-Cubs fans alike. There are lots of bars and restaurants in this area including the super popular Cubby Bear.
Address: 1060 W Addison St.
Cubs tickets
3. Spend the day at Brookfield Zoo
Brookfield Zoo is located about 20 minutes from downtown. Hands down, it is one of the best zoos in the country. I have visited over a dozen zoos across the US and Brookfield remains my favorite – by a large margin. Highlights include: a gorgeous leafy layout, amazing indoor exhibits, a unique underwater bear viewing exhibit & a fantastic dolphin show.
It is an all day experience (the zoo is set on a massive 200+ acres) and you can easily spend hours & hours strolling the beautifully landscaped grounds. My favorite exhibit has always been Tropic World – a world-class indoor primate exhibit. Update: I am excited to visit the new primate habitat which is opening in 2025. You can check out my Brookfield guide for more pics and info.
Address: 8400 W 31st St, Brookfield, IL
4. Relax at Oak Street Beach
Oak Street is a lively beach located on the Gold Coast, easily accessible via the Lakefront Trail and the perfect stop after a long run/bike ride. This beach features the most gorgeous city views and is probably your only chance to ever see a palm tree in the city :-). Volleyball games, big waves, and a cityscape background: what more could you ask for? For a Midwest beach in the middle of the bustling city, consider me impressed!
Address: 1000 N Lake Shore Dr.
5. Walk the Magnificent Mile & State Street
Strolling along N. Michigan Avenue during the summer months is a memorable time with fantastic shopping, restaurants, and scenery along the way. There is so much to do that you can easily make this an all day activity. Some of my favorite stops include: Water Tower Place (an elegant, upscale 7 story mall), Tails in the City (an upscale pet boutique store), Macy’s (it will always be Marshall Fields to us locals!), Fannie May (the iconic Chicago chocolatier), and Burberry.
There are many fancy restaurants lining this street like Michael Jordan’s Steakhouse, Joe’s Seafood, and Shanghai Terrace. More affordable eats include Gino’s East and Lou Malnati’s. One good cheap eat I just discovered recently is Goddess and the Baker. They serve the most amazing pastries and breakfast burritos!
Address: N. Michigan Ave.
Mag Mile directory
6. Take fun reflective pictures at Millennium Park
Great scenery and architecture are the highlights of beautiful Millennium Park, an urban park known for hosting various events and concerts. As the name implies, the park was a celebration of the new millennium. It was supposed to open in 2000, but opening was delayed 4 years. There was a huge multi day festival when it finally opened to the public.
Today, it is a popular venue for all sorts of events. I like coming here most in the winter as it is located right next to the beautiful ice skating rink, although summertime offers an exciting music lineup.
I recommend taking a picture of your reflection by the Cloud Gate sculpture. “The Bean” as all of us locals know it as, is always a hit with new tourists. I love the city views at this park and also all the unique art exhibits.
Address: 201 E Randolph
Check out the attractions and event lineup for the year.
7. Spend the afternoon at Lincoln Park Zoo
Lincoln Park Zoo is a free zoo just north of the downtown area. In fact, it is one of just a handful of remaining free zoos in the US. Really, I have seen some zoos charge more than 30 bucks a person and even upwards of $70 in San Diego’s case, so this is a wonderful deal for city residents and visitors. They don’t require any tickets or reservations either so it’s a hassle-free experience.
Conveniently, the zoo is open 365 days a year. Although I prefer Brookfield, the zoo offers plenty of exhibits and nice views of the city. The indoor primate and lion houses alone justify a visit. What I really love most about this zoo is the spectacular holiday Zoo Lights festival – it’s one of the best. Definitely check it out if you are visiting over the winter season (spoiler: this city is also a fabulous winter destination!).
Address: 2001 N Clark St.
8. Treat yourself to a rainbow cone!
A rainbow cone is a delicious 5 layer ice cream cone (consisting of chocolate, strawberry, NY Vanilla with cherries and walnuts, pistachio, and orange sherbert), and a southside tradition! My favorite flavor is the Palmer House vanilla. The Original Rainbow Cone (which will turn 100 years old in the summer of 2026) is housed in a historic pink building in Beverly, located on Western Ave. – it’s worth the drive!
Although there are now locations around the metro (and even a few locations in IN, WI, AZ, & MI), the original pink building still holds that nostalgia factor for me. I remember at times when the line wrapped around the building. Sadly, I returned in recent years and walked right up to the counter.
Address: 9233 S Western Ave.
Update: I recently tried the Chocolate Obsession (chocolate, peanut butter swirl, cookies and cream, and dark chocolate with a caramel swirl and brownie pieces) at the Dyer, Indiana location. This was almost as good as the original rainbow.
9. Be dazzled by the spectacular Buckingham Fountain Show
I have always thought this is one of the city’s most beautiful landmarks. It is so beautiful, especially at night with the lights and music. The skyline in the background makes for an amazing backdrop for photos. I stop here almost every time I go downtown without getting tired of it. The show runs from 8am-11pm from mid May-October. If you are interested, you can read more about the fountain’s history on the Chicago Park District website.
Address: 301 S Columbus Dr.
10. Attend a summer event
The Windy City offers no shortage of fun events, especially during the warmer months. The Taste of Chicago and free outdoor concerts are a couple of examples of popular events. Summertime in the city is quite a striking difference to the winter season when both locals and tourist tend to avoid venturing out into the cold. Personally, I actually prefer the winter season with the ice rinks and beautiful holiday decorations although I love heading downtown anytime of the year.
No matter what time of the year your visit falls, you will never run out of activities, attractions, or local events. That being said, May-September is the time of the year the city is bustling with tourism and festivals.
My favorite event I ever attended was the 1998 Bulls Championship Rally in Grant Park. This event was so exciting as the Bulls were at their prime with 6 championships throughout the 90’s. It was also the last time Jordan made a speech as a member of the Bulls.
11. Take pics of the skyline by the Alder Planetarium
Chicago is hands down home to the best skyline in the country. You can’t beat the wonderful setting on Lake Michigan. In my opinion, only Pittsburgh and New York City come close. It is one of the best kept local secrets in the city – the best views of the amazing skyline can be taken by the Planetarium! The Adler itself is also worth a visit for the excellent exhibits, stargazing, and shows.
Address: 1300 S Lake Shore Dr.
12. Strike your best pose at the Willis Tower Skydeck
One of the city’s more famous attractions (at the former Sears Tower) is the iconic Skydeck lookout at the Willis. After almost a 10 year wait, I finally got to stand on the Ledge. I can say for sure – yes it’s worth the long wait to strike your best pose (you will see guests doing all sorts of crazy photos).
The glass is just 1.5 inches thick; as you look down 1353 feet beneath you, the city looks so small. You can take some really cool photos and the city views are out-of-this-world. Honestly, I do not think it is a tourist trap despite the hefty price tag.
I also love the memorabilia museum that you will get to stroll through before looking out over the Ledge. You can read a lot of history here and take some fun pics by famous city landmarks. I give them bonus points for marking out the point where Ferris, Cameron, and Sloane looked out at the city on their day off (Ferris Bueller is one of my all time favorite movies!).
Address: 233 S Wacker Dr.
13. Catch a White Sox game
Watching a game at Guaranteed Rate Field (it will always be Comiskey Park to me), you will come across some of the biggest fans in baseball! Locals on the southside really love their team! I have always enjoyed the rivalry between Sox fans (typically on the southside) and Cubs fans (typically on the northside) and even had family members who supported opposing teams.
The field is clean and modern and the fireworks are awesome. Even if you are not a White Sox fan, you will appreciate the atmosphere and enthusiasm of die hard locals.
Address: 333 W 35th St.
White Sox tickets
14. Visit one of the best aquariums in the country
The Shedd Aquarium is amazing; I have visited many other aquariums and none of them come close. It is definitely worth a visit, especially during the hot and humid months where you can escape the sun for a while. The highlight here is the whale exhibit which features 8 belugas.
After you had your fill of fish tanks, I recommend a stroll along the Lakefront Path, heading over to the Magnificent Mile for some shopping, or relaxing at one of the nearby beaches. I recommend a full day out to justify the hefty parking fees. I like to park once and enjoy a variety of activities.
Address:1200 S Lake Shore Dr Chicago, Illinois 60605
Shedd exhibit guide
15. Ride the Ferris wheel at Navy Pier
The views from the famous 196 foot tall Navy Pier Ferris Wheel are amazing and afterwards you can walk around the shops and restaurants. You will find a lot of iconic city treats here including the original rainbow cone, Harry Caray’s Tavern, Giordano’s, and Garrett’s Popcorn (it’s so delicious and they offer so many tempting flavors!). Also, there are a lot of free events here like the summer fireworks series.
This ride is one of the best ways to take in enchanting views of both Lake Michigan and the city. For those on a budget, I recommend a ride as a cheap alternative to the amazing but pricey Willis Tower Skydeck experience.
Address: 600 E Grand Ave (at Illinois St) Chicago, IL 60611
Guide to Navy pier attractions & special events
16. Take a self guided tour of 80’s John Hughes movies
At one point, the city was a very popular filming location. So many great 80’s classics took place in the suburbs. Most famously, John Hughes (a Chicago North Shore native), used the city as the backdrop for most of his iconic films. I am a big 80’s movie fan (I visit filming sites around the US) and I have seen all of John’s movies countless times.
On the Northside, you can visit some of the iconic filming sites like:
- Cameron’s house from Ferris Bueller’s Day Off
- The Baker’s house from Sixteen Candles
- The Mcallister house from Home Alone
- Shermer High School from The Breakfast Club
- Neal’s house from Planes, Trains, & Automobiles
All of these movies filmed in the beautiful North Shore neighborhoods. Being a native, these films always bring me back to my days growing up in the city. I have wanted to tour these houses being a huge fan of all the films. It was so much fun!
17. Treat yourself to some deep dish pizza
There is no best time of year to treat yourself to a slice (or 2 or 3) of amazing deep dish pizza. I am sure almost everyone has heard of Giordano’s, the iconic pizza chain which started in 1974 on the south side. It’s seriously good and should be on your bucket list any time of the year!
I highly recommend the Super Veggie, although they do offer a number of specialty options including: spinach, margherita, and double pepperoni. Thin crust and tavern style also available! On a side note, I also recommend their Greek salad.
18. Take in stunning views from the John Hancock Observatory
The city views from this historic skyscraper’s 1030 foot deck are amazing. Plan your trip on a clear day for the best views. It’s conveniently located on the Mag Mile so there are many shops and restaurant in the vicinity. If you want to splurge, you can make reservations to dine in the popular Signature Room, a fine dining restaurant located on the 95th floor which offers panoramic views of the city.
Address: 875 N Michigan Ave 94th Fl Chicago, IL 60611
19. Explore incredible dinosaur exhibits at The Field Museum
The Field is one of my favorite museums anywhere. The dinosaur and mummy exhibits are both phenomenal. What draws most tourists here is Sue, the largest and most well preserved T-Rex fossil.
Only The Smithsonians in D.C. and The Carnegie in Pittsburgh can really compare to the extensive exhibits found here. I enjoy visiting in the summer months over the winter because the weather is nice enough to walk around and enjoy all the other attractions that the city has to offer.
Going to The Field Museum was always the field trip of the year in my grammar school days and I still have fond memories of the now closed McDonald’s.
Address: 1400 S Lake Shore Dr Chicago, IL 60605
The Field Museum exhibit guide
20. Explore Wicker Park
Wicker Park is a fun and funky neighborhood that is home to a lot of local shops and restaurants. It’s located on the west side of the city just a few miles outside of the downtown. There is metered parking here which I love because I don’t have to pay $20-30 for a garage.
I love the eccentric vibe here and summertime is the perfect time to stroll around without freezing your butt off. Here are a few places I recommend adding to your bucket list:
- The Wormhole: This amazing local coffeeshop serves great coffee and pastries plus the 80’s themed decor is so cool. They have a DeLorean from Back to the Future – how cool is that?
- Myopic: A 3 story used bookstore. This place is massive, so if you love books, you can spend hours exploring.
- Emporium: A trendy arcade bar that serves craft beers.
21. Get back to nature at a preserve
There are plenty of beautiful parks located throughout the city, which are perfect for both recreation and relaxation. One of my favorite places in the suburbs (it’s worth a quick drive for the relaxing setting and beautiful nature trails) is Little Red Schoolhouse in Willow Springs.
While the trails here are quite short, you will get to enjoy a rustic little hike, bird watch, and rejuvenate for at least an hour or 2. You can also tour the first grammar school (a one room schoolhouse built in 1886). There is a big nature center and they often offer guided bird walks and other tours.
Lake Katherine and Morton Arboretum are 2 other great choices.
Address: 9800 Willow Springs Rd, Willow Springs, IL 60480
More info on the Little Red Schoolhouse
If you are willing to take a daytrip (trust me, it’s worth it!), Starved Rock State Park is amazing. It’s an hour and a half drive but the scenery is incredible (especially if you visit after heavy rainfall when the waterfalls are flowing).
There are 18 canyons here (8 of which you can hike to), my favorite being Wildcat (the deepest in the park at 70 ft). The hike is a moderate 2 mile trek which features a stunning 90 foot waterfall (I finally timed my hike just right and got to see a decent waterfall!). Not bad for Illinois!
22. Cool off at The Art Institute
Sometimes on really hot and humid days, heading indoors is your best option. Thankfully, there are so many great museums including a top rated Art Institute. The collection here is stunning: one of the most impressive I’ve seen anywhere.
Some of the famous works you will get to see include: A Sunday Afternoon on the Island of La Grande Jatte, American Gothic, and The Child’s Bath. Another advantage: it’s easily accessible to most other attractions and activities in the city.
If you are a fan of Ferris Bueller’s Day Off like me, you will know that the art museum was one of the places Ferris and friends visited on their day off. The museum now offers a Ferris tour where you can see the impressive art pieces featured in the film.
Address: 111 South Michigan Avenue, Chicago, Illinois, 60603
Exhibit guide and special events at The Art Institute
23. See a show
Chicago is one of the best places to see live theater in America. A hot, humid summer afternoon (a frequent occurrence) is the perfect time to book tickets to a show at one of the city’s world class theaters. Relax in the air conditioning for a bit and enjoy a Broadway or local production.
The Chicago Theater, LookingGlass, and Cadillac Palace are all great options. One of my favorite experiences thus far was seeing Wicked in the early 2000’s at the Oriental Theater (now the James M. Nederlander Theatre).
Address: Various
Check out this guide to upcoming Broadway productions to see if anything interesting is going on during your vacation.
24. Enjoy local eats
This is a city where locals are passionate about their food especially deep dish pizza, hot dogs, Italian beef, Polish food, and Greek food. Portillo’s, and Lou Malnati’s are a few popular tourist favorites. There are now locations across the city and suburbs, so they are super convenient no matter where your day’s adventures may take you.
My favorite local restaurants are Vito and Nick’s Pizzeria (best pizza anywhere) and Fox’s (a local family-run pizza pub with numerous suburban locations). Vito and Nicks’ (on the southside) serves iconic tavern style pizza that is hard to match.
25. Take a scenic boat ride
Nothing says summer quite like some time on the water. You can pick amongst numerous touristy boat rides, from architecture photography cruises to relaxing sunset cruises. In addition, a variety of lunch and dinner cruises take off from Navy Pier.
On a tight budget? The Water Taxi is a budget-friendly & scenic means of transportation which doubles as a sightseeing activity. An all day ticket will only set you back 10 bucks.
