Chicago does not need much of an introduction, but it does reward a little planning. This city stretches 26 miles along Lake Michigan, packs in more than 200 neighborhoods, and somehow still feels walkable once you know where to start. From Cloud Gate and an architecture river cruise to the neighborhoods most first-time visitors skip entirely, here are 35 things to do in Chicago that actually earn a spot on your itinerary.
NEW!
August 12nd 2026 •
15 min read
35 Best Things to Do in Chicago for Every Kind of Traveler
August 3rd 2026 •
14 min read
14 Hidden Gems in Las Vegas Beyond the Strip
July 27th 2026 •
6 min read
100 Things to Do in 100-Degree Heat
May 19th 2026 •
16 min read
72 Fun Things to Do on Father's Day in 2026
February 24th 2026 •
17 min read
Things to Do in California: Explore the Best Experiences
February 2nd 2026 •
20 min read
49 Fun & Romantic Things to Do on Valentine’s Day
September 20th 2025 •
10 min read
Your Ultimate New York City Adventure: Hidden Gems, Things to Do & Memorable Gifts
June 17th 2025 •
8 min read
45 Fun Things to Do with Friends Near Me That Actually Live Up to the Hype
June 3rd 2025 •
6 min read
The Best Things to Do in Miami with Kids (That You’ll Actually Want to Do Too)
May 14th 2025 •
7 min read
32+ Fun Things To Do After Graduation That Are Way More Exciting Than a Cake and a Card
May 8th 2025 •
5 min read
26 Fun Outdoor Activities for Adults That Aren't Just Walking
April 9th 2025 •
11 min read
Unique Things to Do on Mother's Day: Unforgettable Activities & Gift Ideas
March 13rd 2025 •
9 min read
20 Fun and Memorable Things to Do with Your Grandparents
March 10th 2025 •
14 min read
Top Things to Do in Dallas: Your Ultimate Guide
February 17th 2025 •
10 min read
Top 50 Things to Do With Girlfriend: Ultimate Date Ideas
January 2nd 2025 •
19 min read
Top 36 Things to Do with Your Boyfriend
April 9th 2024 •
14 min read
Best Things to Do in San Diego: 60+ Exciting Activities
March 21st 2024 •
16 min read