So you’re planning a trip to Chicago, huh? Look no further! I’ve compiled a list of my favorite must-do activities during your stay in the Windy City!
My very first Travel Med Tech contract was to Chicago! I was lucky enough to spend 6 months in this beautiful city and I’d love to share my favorite adventures!
I was in Chicago from January 2022 to June 2022 so I got to experience the city in the winter AND the summer, and let me tell you- it was 2 completely different worlds! While the winter months were brutal- the wind makes it SO much colder- the city is beautiful covered in snow and is much less crowded than in the summer. So if you can brave the cold, Chicago in the winter is a must! However….. Chicago in the summer is something else. The city comes alive, the riverwalk shops and restaurants are open, there are boats on the lake and people on the beach. I love Chicago in the summer! That being said, the things on the list below can all actually be done in the winter OR the summer (minus 1). So choose the time to visit that works best for you- there’s no wrong time to visit!
#1- The Magnificent Mile
The Magnificent Mile- or “the Mag Mile”- is an upscale area of Chicago’s Michigan Avenue. The Mag Mile has it all- from luxury shopping (over 450 retailers!) and restaurants, to historical landmarks- including the Wrigley Building, the Tribune Tower, and the Drake Hotel to name a few- and the largest Starbucks roastery in the world! The Magnificent Mile is a must see when you visit Chicago.
**Note- I recommend starting at the top of the Mag Mile on Oak Street and working your way south towards the Chicago River. Don’t miss out on a chance for photos at Oak Street Beach! The contrasting views of the beach against the Chicago skyline are breathtaking!
#2- Riverwalk
The end of the Mag Mile puts you right at the Chicago River, so continue your walking journey down to the riverwalk where there are more shops, restaurants, and amazing views! You’ll see the Trump Tower along with many other amazing architectural feats.
#3- Kayaking the Chicago River
Clearly this is a summer activity, but if you have the chance, I HIGHLY recommend a kayak tour. I booked a sunset, architecture tour and it was one of the best adventures I’ve ever been on! The skyline, the sunset, and the kayaking itself were all amazing! It was approximately a 2 hour tour with Urban Kayaks and the guide was super knowledgeable! Click here for more info on the different kayak tours Urban Kayaks offers!
**I’d like to point out that this was my first time ever kayaking and I got along just fine, so don’t let that stop you!
#4- Cloud Gate (a.k.a. The Bean)
The Cloud Gate is a 110 ton piece of art that was added to the Chicago skyline in 2004 and attracts millions of people every year to its reflective surface! This iconic Chicago structure is found in Millennium Park and is free to all visitors!
#5- Chicago Theater
Take a stroll past the Chicago Theater, or better yet, get yourself tickets to a show! What better way to spend an evening than seeing a show at one of the most historical theaters in the country!
#6- Navy Pier
Navy Pier is home to many restaurants, shops, and adventures. You can’t miss the Centennial Wheel! The views of Chicago’s skyline from Navy Pier are awesome as well!
#7- Wrigley Field
Grab a beer and a hot dog and watch the Chicago Cubs play baseball at the infamous Wrigley Field!
#8- Field Museum of Natural History
If you enjoy art, science, and history, you CAN’T miss the Field Museum of Natural History. Home to numerous exhibits, you’ll find dinosaurs, mummies, ancient civilizations, and more. There’s no shortage of exciting displays! The Field Museum is also home to Sue- the world’s largest and most complete T-rex skeleton- so cool!
**Click here for more info regarding the Field Museum of Natural History!**
#9- Skydeck Chicago
Get your adrenaline pumping by standing in a clear box 103 stories above Chicago! Located in Willis Tower, the Skydeck offers spectacular views of Lake Michigan, the city, and the suburbs beyond- spanning over 50 miles! Included in ticket prices are a museum experience (history of the L train, famous Chicago historical figures, architectural facts, and more), the skydeck views, and the Ledge. This was one of my favorite activities! Click here for more info regarding the Skydeck Chicago experience!
#10- The Green River
If you’re in Chicago during St. Patrick’s Day you HAVE to make a trip to the riverwalk. The river gets dyed green for the holiday and it’s a must-see for sure! It was one of my favorite experiences during my time in Chicago!
**Psst! If you buy a Chicago City Pass, you can save up to 48% on admissions/tickets to some of Chicago’s most exciting attractions!
There you have it. 10 MUST-DO things during your trip to one of the most exciting cities in the U.S.! Let me know if you go on these adventures on your next trip to Chicago! Have fun in the Windy City!
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