I just got home from Chicago and having a small heart ache from being away. Here are some of my recommendations for a long weekend trip.
Sections
3
Places to visit
Places to eat
The details
Places to visit
Great central location, super clean, very kind staff. Don’t sleep on the water in the downstairs lobby either! So refreshing
The Royal Sonesta Chicago River North - Official Website
Super fun if you haven’t tried kids along, if its just adults, I would probably skip
MUSEUM OF ICE CREAM
This is a fun 90 minute trip. The guides are funny, and you learn a ton of history, plus you get to see amazing architecture. Make sure to take a poncho if it rains, or buy one at the bar, so you dont miss out on the history.
Chicago River Boat Architecture Tours
Tons of everything you might need and fun open air carnival.
Navy Pier
This place is huge! I would break it into 2 days if you aren’t a huge art enthusiast but appreciate original art and tons of artifacts.
The Art Institute of Chicago
Even if you aren’t a baseball fan, you don’t want to skip this
Wrigley Field
The bean, the fountain, don’t skip.
Millennium Park
Who doesn’t love the beach in the middle of the city? Being from the west coast, I was amazed at this Great Lake.
Chicago Beaches | Guide to Local Beaches on Lake Michigan
This was my favorite place to stop. You get 90 minute table time but we were able
To just walk in. The cheese curds were delish and so were the drinks. This felt like a real hidden speakeasy not something advertised all over.
Experience the Best of Chicagos Historic Speakeasies at The Drifter - Book Now
Fun little dive bar.
The Green Door Tavern
We didn’t make it to this, but trust me it’s my first stop next trip.
Drunk Shakespeare
Places to eat
The biggest starbucks in the world. Super cute, fun and funky drinks and food you can’t get anywhere else. Try the ube coconut latte and the lemon strawberry tart and thank me later.
Starbucks Reserve Roastery
So much fun merch, plus you can order dessert and butterbeer. Its a little spendy but you get a souvenir cup(they even have a wash station so you aren’t carting a sticky cup around)
Harry Potter Shop Chicago
Super yummy chicago mix. You can send tins home if you don’t want to finagle it on the plane but you have to do it online. The strawberry lemonade is to die for
Garrett Popcorn Shops
Good donuts, good coffee and we even tried a ham and cheese pretzel that was wonderful. Price was also good.
Stan's Donuts & Coffee
Excellent deep dish, and if you haven’t tried it, you have to. There is also a sister restaurant across the street if its too busy, called Due! Clever! Excellent service. The pizza takes 45 minutes to cook so they will take your order when they put y...
Pizzeria Uno
The location looks sketchy from the outside but its a Chicago must! You can order a Chicago handshake which is a hamburger, beer and shot of malort, another Chicago must.
Billy Goat Tavern (The Original)
We got an Italian Beef Sandwich and a Chicago Dog and halved them to share. Great price, and a fun restaurant to knock out two Chicago staples.
Portillo's & Barnelli's Chicago
If you are a fun of The Bear you can’t miss this stop.
Mr. Beef | Sandwich Shop in Chicago, IL
This was the bar attached to our hotel and we ate there 2 times. Probably the best burger I have had and the yummiest truffle fries. Trust me, order the churro cake
CBR
The details
The train was a little overwhelming at first but a nice citizen stopped and gave us some tips. Super clean and easy to navigate
Maps - CTA
Seriously the easiest city to navigate and walk everywhere! We were never uncomfortable or felt unsafe the whole time we were there. Day or night.
How walkable is Chicago? : r/AskChicago
Plan on being there 3 hours early, its big and crowded and slow to get anywhere.
