Planning a trip to Chicago in 2026? In this video, we explore 15 of the best things to do in Chicago, from iconic landmarks and stunning architecture to incredible viewpoints, neighborhoods, attractions, and experiences you shouldn’t miss.
Whether you’re visiting Chicago for the first time or looking for new places to explore, this Chicago travel guide will help you discover the best things to see and do in the city.
From the Chicago Riverwalk and Millennium Park to Willis Tower, Navy Pier, the Magnificent Mile and more, these are some of the top experiences to add to your Chicago itinerary.
CHICAGO TRAVEL GUIDE 2026
15 Best Things to Do in Chicago
Best Places to Visit in Chicago
Chicago Attractions
Chicago Travel Tips
Chicago Itinerary
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CHAPTERS:
0:00 Intro
0:42 #15 Millennium Park
1:28 #14 The Chicago Riverwalk
2:13 #13 The Chicago Lakefront
3:00 #12 The Art Institute of Chicago
3:46 #11 Grant Park & the Museum Campus
4:33 #10 The Loop & Chicago Architecture
5:20 #9 The Food
6:09 #8 The Magnificent Mile
6:55 #7 Chicago Blues & Jazz
7:41 #6 Wicker Park, Logan Square & Pilsen
8:30 #5 Wrigley Field
9:12 #4 Chicago at Night from the Water
9:58 #3 Indiana Dunes National Park
10:42 #2 Live Blues at Buddy Guy’s Legends
11:18 #1 Chicago Itself
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Cool video. A couple of minor nitpicks. Blues and Jazz make the list, referencing Buddy Guy’s. But then Buddy Guy’s Place itself captures #2 on the list. While this isn’t my list, I think the earlier ranking of Blues and Jazz was good enough. I’ve been to Buddy Guy’s and had a great time, but it’s a bit too niche for a #2 ranking. Also, there were two incorrect b-roll clips. One that showed the John Hancock building instead of the Willis (Sears) Tower and another that showed Gold Coast/Rush and State while referring to West Loop. Appreciate the shoutouts of other neighborhoods like Logan Square, Pilsen and Wicker Park. I always suggest people to visit those areas if they can. Indiana Dunes is also a bit of a stretch. I’d only recommend it if you’re visiting for a good four or five days.
It is an excellent video about a wonderful city. The footage at 9:54 is spectacular and is an ideal representation of Chicago. Personally, I would have put number 14 at number 2. The Chicago skyline has a gorgeous shape; many skylines are a random cluster of buildings. We visited Chicago recently and were impressed by how clean the downtown area was. The streets and sidewalks were almost spotless, and the major park (Grant Park) had no litter or tents. Chicago has the most impressive downtown core outside of Asia. Also, number 1 is apt: Chicago has a soul. John Hughes made a movie (Ferris Bueller's Day Off) and he said "I wanted the movie to show the spirit of Chicago," and Chicago does have a spirit. Chicago is perfect for a 3 night / 2 day vacation. NYC is splendid, but one needs at least 5 days there. Many of us work a lot and have trouble getting time off for a vacation; Chicago is terrific for a weekend. Lastly, to the MAGA crowd: Chicago had 416 murders in 2025, the lowest amount since 1965. Most of the violence in Chicago was in destitute neighborhoods, that a tourist would not go to.
Visited Chicago for the first time 3 years ago and I've been wanting to go back ever since. Amazing city!
One "attraction" that was not on the list but is a personal favourite of mine as it was a big part of my childhood growing up, especially around Christmas time, is visiting the Home Alone house. It was one of the main reasons I visited Chicago in the first place.
I will definitely be visiting Chicago again. Hopefully soon!