Top Ten Travel List Logo Show Mobile Menu

25 Fun Things to do in Chicago this Summer

Chicago Skyline

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

3. Spend the day at Brookfield Zoo

Brookfield Zoo is located about 20 minutes from downtown Chicago in the town of Brookfield. One of the best zoos in the country with a gorgeous 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 has 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 pictures at Millennium Park

Great scenery and architecture are the highlights of a visit to Millennium Park. Taking a picture of your reflection by the Cloud Gate sculpture is always an entertaining experience. 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.

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

Cloud gate at Millennium Park - Chicago


  1. Chicago is a great city.

  2. Thanks for letting me know! I have updated the link 🙂

    • Kyryll
    • June 21, 2014  at  7:05 AM

    Great stuff. But Hancock Observatory had moved to a new domain Could you adjust the links please?

  3. Chicago is a great city with too many great attractions to fit into just one visit! A limo is a great way to travel with style through this great city 🙂

    • Elsam
    • March 1, 2014  at  5:26 PM

    Thank you very much for publishing such resourceful blogs about tourism. What a nice opportunity to know about the beautiful tourist spots and lodging options. It is opportunity to aware our visitors who used our services of luxurious Limousine during their vacations.

  4. […] you liked this post, then take a look at Fun Southern California Beaches!, Summer in Chicago: 25 Things to Do!, and Beach Vacation […]

Travel With Us!