Best things to do in Chicago this summer - Chicago skyline views from Adler Planetarium

Chicago is one of the best summer cities! There are so many events, festivals, and beautiful places to explore, making it the ideal summer destination city. Having once lived in Chicago for over 20 years, I have had plenty of summer adventures over the years. Whether you are in a mood for fitness, museums, food, or entertainment, you are bound to find something to suit your interests. Check out my list below. What are some of your favorite Chicago attractions and activities?

1. Walk/bike the Lakefront Trail

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. Some of my favorite stops along the way include Oak Street Beach, The Field Museum, Lincoln Park Zoo, and the Planetarium for the amazing skyline pictures!

Address: 1600 N Lake Shore Dr. Chicago, IL 60657
More info on the Chicago Lakefront Path

Views of the skyline from the Chicago Lakefront Path

2. See a Chicago Cubs game

Watching a Cubs game at Wrigley Field is always a fun experience. I recommend sitting in the bleachers for the most authentic experience! The post game bar scene in Wrigleyville is entertaining for both Cubs and non-Cubs fans alike. Take this opportunity to visit the second oldest ballpark in the country (next to Fenway!). An interesting fact: The Chicago Bears used to play at Wrigley Field before they had Soldier Field!

Address: 1060 W Addison St, Chicago, IL 60613
Chicago Cubs tickets

Chicago Cubs game at Wrigley Field

3. Spend the day at Brookfield Zoo

Brookfield Zoo is located about 20 minutes from downtown Chicago. Hands down, it is one of the best zoos in the country! Highlights include a gorgeous leafy layout, amazing indoor exhibits, a unique underwater bear viewing exhibit & a fantastic dolphin show. Brookfield 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.  Make sure to visit Tropic World, an amazing indoor primate exhibit!

Address: 8400 W 31st St, Brookfield, IL 60513
More info on Brookfield Zoo

Dolphin show at Brookfield Zoo - Chicago

4. Relax at Oak Street Beach

Oak Street is a fun 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 gorgeous city views! Oak Street is probably your only chance to ever see a palm tree in Chicago :-). Volleyball games, big waves, and a cityscape background: what more could you ask for out of a Chicago beach?

Address:  1000 N Lake Shore Dr  Oak Street Beach, IL 60611
More info on Oak Street Beach

Oak Street Beach- Chicago

5. Walk the Magnificent Mile

Strolling along N. Michigan Avenue during the summer months is a memorable time with fantastic  shopping, restaurants, and scenery along the way. 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, and Burberry.

Address: N. Michigan Ave. Chicago, IL 60611
More info on the Magnificent Mile

Magnificent Mile Chicago

6. Take fun reflective pictures at Millennium Park

Great scenery and architecture are the highlights of beautiful Millennium Park. Taking a picture of your reflection by the Cloud Gate sculpture, “the bean” is always an entertaining experience for new tourists. The central park is also the site of numerous summer events and concerts. Numerous photography opportunities await you as you are surrounded by stunning architecture and sculptures in every direction. If your visit falls during the winter months, you will want to check out one of the country’s best (and only free) urban ice rinks.

Address: 201 E Randolph  Chicago, Illinois 60602
More info on Millennium Park

Cloud gate sculpture at Millennium Park - Chicago

7. Spend the afternoon at Lincoln Park Zoo

Lincoln Park Zoo is a free zoo just north of the downtown area. In fact, Lincoln Park is one of the 3 remaining free zoos in the US! Although not as large as Brookfield, the zoo offers plenty of exhibits and nice views of the city. The indoor primate and lion houses are well worth the visit alone. If visiting during the winter months, do not miss out on the amazing holiday Zoo Lights spectacular.

Address: 2001 N Clark St, Chicago, IL 60614
More info on the Lincoln Park Zoo

Cute pic of lion sleeping at Lincoln Park Zoo - Chicago

8. Treat yourself to a rainbow cone!

A rainbow cone is a delicious 5 layer ice cream cone (chocolate, strawberry, NY Vanilla with cherries and walnuts, pistachio, and orange sherbert), and a Chicago tradition! The Original Rainbow Cone is housed in a historic pink building in Beverly, located on the Southside of Chicago – it’s worth the drive!

Address: 9233 S Western Ave, Chicago, IL 60643
More info on the Original Rainbow Cone

9. Be dazzled by the spectacular Buckingham Fountain Show

This fountain is beautiful, especially at night with the lights and music. The skyline in the background makes for an amazing backdrop for photos. I stop here every time I go downtown without getting tired of it.

Address: 301 S Columbus Dr Chicago, IL 60605
More info on Buckingham Fountain

Buckingham fountain in Chicago, Illinois

10. Attend a summer event

Chicago offers no shortage of fun summer events. The Taste of Chicago and free outdoor concerts are a couple of examples of popular summer events. Chicago is a lively city, especially during the summer months. You will never run out of activities, attractions, or local events! This time of the year the city is bustling with tourism and festivals.

Upcoming summer festivals

Grant Park in Chicago, IL

11. Take pics of the skyline by the Alder Planetarium

It is one of the best kept secrets in the city- the best views of the skyline can be taken by the Planetarium! The Planetarium itself is also worth a visit for the excellent exhibits and shows!

Address: 1300 S Lake Shore Dr  Chicago, IL 60605
More info on the Adler Planetarium

Skyline views from the Adler Planetarium in Chicago

12. Shop at Water Tower Place

This 7 floor Michigan Avenue mall is just amazing. The elegant design, variety of shops, and central location on the Magnificent mile make it an ideal destination for anyone looking for an amazing city shopping destination.

Address: 835 N Michigan Ave, Chicago, IL 60611
More info on Water Tower Place

Water Tower Place Chicago

13. Catch a White Sox game

Watching a game at US Cellular field, you will come across some of the biggest fans in baseball! Locals really love their team! 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, Chicago, IL 60616
White Sox tickets

14. Visit one of the best aquariums in the country

The Shedd Aquarium is amazing; I have visited several other aquariums that do not even come close! It is definitely worth a visit, especially during the summer! What a great cool escape on a hot and humid afternoon! You can walk around outside along the Lakefront Path when you are done, head over to the Magnificent Mile for some shopping, or visit one of the nearby beaches.

Address:1200 S Lake Shore Dr  Chicago, Illinois 60605
More info on the Shedd Aquarium

The Shedd Aquarium in Chicago, Illinois

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. This is one of the best ways to take in enchanting views of both Lake Michigan and the city! Cheaper than the Willis Tower skydeck, yet still amazing!

Address: 600 E Grand Ave (at Illinois St) Chicago, IL 60611
More info on Navy Pier

Navy Pier in Chicago, IL

16. Enjoy a local festival

Chicago has an abundance of festivals going on just about everywhere all summer season long. These festivals always include great food, great drinks, and great entertainment. I enjoy attending these events because I can always find a Rainbow Cone stand – one of my favorites! (see number 8 above). From food festivals, to parish carnivals, to free concerts, there is something going on in the city and suburbs on any given weekend.

Chicago suburbs festival guide

17. Take advantage of seasonal outdoor concerts

Millennium Park is one of the hotspots for summer concerts, offering a series of freebies all summer long. In addition, various locations throughout the city and suburbs host concerts and festivals throughout the summer months.

Millennium Park Summer Concert Series

Milennium Park - Chicago

18. Take in stunning views from the John Hancock Observatory

The city views from this historic Magnificent Mile skyscraper are amazing! Plan your trip on a clear day for the best views! Another option is to dine in the popular Signature Room on the 95th, a fine dining restaurant located on the 95th floor, complete with panoramic views of the city.

Address: 875 N Michigan Ave 94th Fl Chicago, IL 60611

More info on the John Hancock Observatory

John Hancock Building in Chicago, IL

19. Explore incredible dinosaur exhibits at The Field Museum

The Field is one of my favorite museums in Chicago. The dinosaur and mummy exhibits are both phenomenal. 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.

Address: 1400 S Lake Shore Dr  Chicago, IL 60605
More info on The Field Museum

The Field Museum Chicago

20. Enjoy a summer picnic in the park

Enjoy the warm summer air & fresh breeze as you take in gorgeous views of Lake Michigan. Almost every stop along the Lakefront Path is ideal for a picnic.

Check out the expansive selection of parks in the Chicago Park District

Beautiful scenery along the Chicago Lakefront trail

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. A little trek outside of the city (but worth it for the relaxing setting and beautiful nature trails) is Little Red Schoolhouse in Willow Springs.

Address: 9800 Willow Springs Rd, Willow Springs, IL 60480

More info on the Little Red Schoolhouse

Little Red Schoolhouse is the perfect place to escape the city congestion for a peaceful day of trails, picnics, and lake views!
Little Red Schoolhouse is the perfect place to escape the city congestion for a peaceful day of trails, picnics, and lake views!

22. Cool off at The Art Institute

What better way to cool off on a hot, humid Chicago afternoon than a trip to The Art Institute of Chicago? The collection here is stunning: one of the most impressive in the country. Another advantage: it’s easily accessible to most other attractions and activities in the city.

Address: 111 South Michigan Avenue, Chicago, Illinois, 60603
More info on The Art Institute of Chicago

The Art Institute of Chicago

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 visit one of Chicago’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.

Address: Various

Upcoming Broadway productions

Wicked at The Chicago Theater

24. Test out a local restaurant (or two)

Chicago is a city where locals are passionate about their food. Chicago is known for deep dish pizza, hot dogs, Italian beef, Polish food, and more. Portillo’s, Lou Malnati’s, and Giordano’s are a few popular tourist and local favorites. I have listed the address below for the city locations (you can also find locations spread throughout the suburbs).

Portillo’s Chicago
Address: 100 W Ontario St  Chicago, IL 60654

Lou Malnati’s
Address: 1120 N State St Chicago, IL

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).

25. Take a scenic boat ride

Nothing says summer quite like some time on the water. Chicago offers no shortage of 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 Chicago 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.

More info on the Chicago Water Taxi

Boat ride views on The Chicago Lakefront Path

What are some of your favorite summertime activities in Chicago?