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Chicago Anti-List (A Trip planned for my Mortal Enemy)
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items There's a high likelihood I'm moving back to my favorite city (Chicago) and I already feel like I know the city backwards and forwards. How many lists could I possibly make about that city? It got me thinking, how would I plan an “Anti-List”? Where w...
Sections
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Eat Here (If You Want to Regret It)
Visit These Places (If you Enjoy Wasting Your Time)
Where You Should(n't) Stay
What You Should Try Instead!
Eat Here (If You Want to Regret It)
Chicago is a fantastic food city, it really is. I might ruffle some feathers- sorry if you find your fave on this list!!
Why is there always a line here when I walk by. Out the door! I feel like Nutella went ‘viral’ like 20 years ago! Not that nutella isnt good…but you can add nutella to anything you want anytime you want- why waste a morning in this fantastic city her...
Nutella Cafe Chicago
HOT TAKE. I KNOW! Look, if you love Starbucks, then hey by all means. But if you're visiting the city and you just want a morning cuppa- there are sooo many better independent coffee shops you should visit instead
Starbucks Reserve Roastery
You'll find locations of these all over. They're sort of perfect for a corporate lunch. but thats just it, its nothing special. Especially after they changed how they make everything! Just go straight to the source- Au Cheval.
Menu » Signature Burgers | Golden Fries | Ice Cream
Every tourist who comes here, undoubetdly wants to eat deep dish pizza. And I get it! I wont go are far as to say I dont like it. I just think its overhyped
The History of Chicago Deep-Dish Pizza
Its…fine? Its just sort of resting on its ‘name’ and laurels right now- not the quality of the menu
Billy Goat Tavern - Chicago
Visit These Places (If you Enjoy Wasting Your Time)
Waste of time is maybe harsh. But these places are certainly….a one and done for me
I am really nottt a fan of the Instagram-y type museums. Do they have some cool stuff? Sure, yes. take your pictures by all means. But its definitely a one and done for me.
Chicago: Balloon Museum - EmotionAir - Entry Tickets
If I REALLY hated someone. I'd just take them to Lower Wacker, point to something and shout “look over there!” and run.
Lower Wacker Drive
If you are a first time visitor to Chicago, there is zero doubt you'll end up here. Its not that its bad…its just that its literally just a street. A street with shops. Shops that exist in every other major city lol.
Magnificent Mile
Another hot take because this event is beloved. But I find the food to be overpriced, lower quality than just getting it straight from the source. Plus its hot and crowded!
Taste of Chicago
ANOTHER instagrammy museum. I think you're getting the idea by now…
Chicago: Museum of Ice Cream Entry Ticket
Its not..bad per say. I mean on one hand, I'm pretty sure you'll see Navy Pier listed on every “overrated” Chicago attraction list ever. But also Ijust wish it was more….I dunno..impactful? Its just…fine
Navy Pier
Where You Should(n't) Stay
I'm very very sorry to the places included on this list. I have my reasons
Unless you're stuck in Chicago because of a flight change or something - I would never recommend staying this close to the airport (or this far from the city)
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Hotel Zachary is NOT a bad hotel lol. I would just not stay here unless you're a massive cubs fan and in town for a game. If you're just here? The crowds in Wrigleyville probably wont be your thing
Hotel Zachary, Chicago, a Tribute Portfolio Hotel
Naperville isnt chicago lol
THE 10 BEST Hotels in Naperville, IL 2026 (from $66)
What You Should Try Instead!
Obviously I wouldn't leave you all hanging!!
I will literally never NOT recommend the Chicago Boat Architecture tour. Its my favorite thing!
Chicago River: 1.5-Hour Guided Architecture Cruise
I mean obviously I was going to include my own list- some more Chicago favorites!
A Cool Girls Guide to Chicago
A super underrated museum- sometimes forgotten because its not in the museum campus. But not one to be missed imo!
Chicago History Museum
Thin crust is actually where its at. I also love Coalfire!
PIZZ'AMICI
Is it kind of touristy, of course. But its a beautiful way for a nice walk and a nice view. I never get sick of it
Home - Chicago Riverwalk
Go here (if you can get a reservation!)
Armitage Alehouse
My list for Chicago over the holiday season!
A Cool Girl's Guide to a Perfect Chicago Holiday Weekend