If you’re planning a long weekend trip to the Windy City and aren’t quite sure what to do, keep reading for our epic 3 days in Chicago itinerary!
While Chicago is the 3rd-largest city in the US, it’s often overlooked by travellers who jet for one of the coasts.
In my opinion, Chicago is the best city in the country. New York and LA are great and all, but I’ll gladly take the friendly Midwestern vibe of Chicago instead.
Situated on Lake Michigan, the Chicago skyline is one of the most beautiful in the world. After all, it was here that the first skyscraper was built in 1885!
There’s so much going on here that you could spend a lifetime there and never run out of things to do.
With a solid Chicago itinerary, you can definitely check out the best of the city in 3 days. Let’s get to it!
How to Spend a Perfect 3 Days in Chicago Itinerary
Our 3 days in Chicago itinerary includes:
- Millennium Park
- Shedd Aquarium
- Skydeck Chicago
- Field Museum
- Adler Planetarium
- Art Institute of Chicago
- 360 CHICAGO Observation Deck
- Navy PierMuseum of Science and Industry
- Ferris Wheel
- Crown Fountain
- Cloud Gate
- Willis Tower
- Grant Park
- Magnificent Mile
- Lincoln Park
Looking for more awesome things to add to your Chicago itinerary? Be sure to read our guide to the best things to do in Chicago!
Travel Tips for Visiting Chicago
When to Visit Chicago
The first step in figuring out what to do during your 3 day Chicago itinerary is planning when you’ll visit.
Winter in Chicago can be painfully cold, which can definitely put a damper on your trip. Unless you enjoy frigid temperatures and cold, biting wind, I recommend skipping out on December-March.
Your best bet is to visit Chicago between May and October. It gets hot and crowded in the summer, but there’s so much going on that it’s worth dealing with those minor inconveniences.
Chicago CityPASS
Another huge tip I have before you visit Chicago is to purchase a Chicago CityPASS.
Essentially this is just a multi-use ticket that actually saves you a bunch of money (50% to be precise!) on many great Chicago attractions.
You buy the pass for USD$109, and it includes access to the following:
- Shedd Aquarium
- Skydeck Chicago and
- Field Museum
- Adler Planetarium or the Art Institute of Chicago
- 360 CHICAGO Observation Deck or the Museum of Science and Industry
Best of all, those entrances are mostly express or premium tickets included with the CityPASS, meaning it not only saves you money but saves you time as well.
We highly…
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