Activity Day/Date Ideas
- Water taxi to Chinatown > Dim Sum > walk in Tom Ping Memorial Park
- Riverwalk > Drinks @ City Winery or Tiny Tap > London House / Beatnik / Gibson’s Italia
- Cloud Gate > Art institute > games + drinks @ Chicago Athletic Association > food @ Cindy’s
- Northerly island > Sunset @ Adler Planetarium Skywalk
- MOCA > High tea @ Ritz > Shopping on Mag Mile, Oak St, and Watertower Place > IPizza @ Lou Malnati’s
- Pizza @ Paulie G’s > games @ Emporium > ice cream @ Margie’s candies or Ava’s Italian Ice
- Aire Ancient Baths (book the first or last time slot of the day to minimize crowd)
Favorite Places
Vibes + views
- London House - probably the best rooftop view in the city
- Cindy’s - same building as the Chicago athletic association
- Virgin Hotel
- Gibson’s Italia - great view, food, and drinks
Bars with Games
- Chicago Athletic Association - swanky spot with fun games
- Punch Bowl Social - not my favorite vibes but they have every game ever made
- Emporium West Loop or Logan Square Logan Square- barcade
- G Cue - billiards in West Loop
Nightlife
- Federales - definitely go definitilythrow an icem shot at the bell
- Blind Barber - gets rowdy AF
- Boozebox - Japanese speakeasy, my favorite bar in the city, late night spicy tuna, great cocktails, good japanese whiskey list
- Lazy Bird - great cocktails and live music
- Esco - more clubby
- Lone Wolf - dark bar with cheap drinks on Randolph, I always end up here late night
- The Bassment - maybe my favorite “going out” spot, always great live music
Outdoors
- Northerly island
- Riverwalk / Lakeshore
- Architecture tour
- Farmers market
- The Playpen
- Water taxi
- Street festivals
- Humboldt park
- Lincoln Park & Lincoln Park Zoo
- The 606
- Chicago Botanic Gardens
- Tom Ping Memorial Park
- Adler Planetarium Skywalk
Food
- Pizza
- Peaquods - pan pizza, best “deep dish”
- Paulie G’s - great thin crust
- Lou Malnati’s - chicago classic
- Dim sum - Chicago’s Chinatown is legit AF
- Asia on Argyle - Where you’ll go for all the Southeast Asian food
- Tacos
- Taqueria Chingon - come for the tacos, stay for the churros. each person needs their own churro order
- Mexican grocery store - good cheap tacos on a grill in the back of a grocery store
- Xocome Antojeria - best mexican food I’ve ever had
- Middle eastern bakery
- High tea - very demure, very cutsie
- Ice cream
- Margie’s candies - it’s a chicago classic, definitely a vibe, was on the bear
- Ava’s Italian Ice
- Akahoshi Ramen - make a reservation a head of time, definitely worthwhile
- Duck Duck Goat - maybe my single favorite restaurant in Chicago
- Bang Bang Biscuits & Pies - one of my favorite brunch spots
- Tortello - best pasta you’ll find anywhere
- Boqueria - bomb tapas restaurant in West Loop that you can pretty much always get into without a reservation
- Mama Delia - Spanish restaurant in wicker
- Amaru - pan Latin food in wicker
Museums
- Art institute
- MOCA
- SHED Aquarium
- Field Museum
- Museum of science and industry
- Adler planetarium
- Chicago architecture center
Shows
- Second city - improv theater that launched the careers of basically every major SNL star, worth a stop for sure
- Steppenwolf Theatre Company - great local theater with good plays
- Civic Opera House
- Chicago Symphony Orchestra
Hotels
- The Hoxton
- The Emily
- Soho House
- Residence Inn
- Marriott Mag smile
- Thompson
- Hyatt House
- The Robey
- Chicago Athletic Association
Spa
- Aire Ancient Baths - my favorite spa in Chicago, great for couples, very romantic
- Red square