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Our local recommendations

We've handpicked our favourite local spots so you can continue exploring like a local after your experience is over.

Our top 5 street food / quick food stops:

Red Hot Ranch – no frills counter service hot dogs and burgers, loved of locals
Mr Beef – cash only Italian beef stand in Chicago featured in “The Bear” on Hulu
The French Market- European-inspired indoor food market for grab-&-go meals, fresh produce & specialty kiosks
Portillo’s – the best of Chicago street food, pasta, and ribs all under one roof
Small Cheval – burgers and milkshakes

Our top 5 most recommended restaurants / food establishments:

Shaw’s Crab House – steak and seafood joint serving the best meals in town
Twin Anchors – prohibition era dive bar serving ribs since 1932
Jibaritos Lincoln Park – comfort food showing off Chicago’s Puerto Rican roots
JP Graziano – 3rd generation sandwich shop and Italian grocer in West Loop
La Scarola - Italian eatery in classic digs surrounded by bars and restaurant

Best coffee stops in the city to start your day:

Do Rite donuts – fantastic donuts and coffee
Big Shoulders coffee – local Chicago coffee roaster
Starbucks Reserve Roastery – one of the largest Starbucks in the world with unique offerings

Top 5 live music / evening entertainment venues you can’t miss:

The Green Mill – jazz club on the north side with live music nightly
The Second City comedy club – improv comedy and live shows
The Second City comedy club – improv comedy and live shows
Andy’s Jazz Club- live jazz featured in a classy, intimate lounge offering dinner
The Bassment - Hip, clubby spot featuring upscale plates, craft cocktails & live blues in moody, underground digs

Our top 3 parks to wander and relax in:

Millennium Park
Lakefront Trail
Lincoln Park and Zoo

Top 5 must-do activities in the city:

Skydeck Ledge – highest observation deck in USA on 103rd floor
Wrigley Field – iconic baseball park from 1914 in a lively neighborhood, catch a Cubs game if the team is in town
Art Institute of Chicago - Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries
Architectural boat cruise – wendellaboats.com
Local theater. There are storefront theaters all over Chicago that do amazing work, both with original works and revivals of Broadway classics

Our favourite hidden gems:

The Pilsen Neighborhood - Popular eateries range from Mexican to Italian, while hip Pilsen Yards and Thalia Hall are great for music lovers
Andersonville – neighborhood on North side with lots of food, drink, culture, and energy
Margie’s Candies - part candy store and part sit-down ice cream parlor

Helpful tips while visiting:

Rush hour traffic – don’t call your Ubers for 3pm to the airport, take the train!
Giordano’s and Pequod’s (overrated for deep dish)
Staying downtown only, you’ve got to get out to the neighborhoods
Segway tours – lame, do a walking tour and get to meet people
Not bringing a jacket, DO bring a jacket – it’s always colder by the lake

Final suggestions on what else to see or do in the city:

Use public transportation! It's easy once you get the hang of it and it will save you lots of money and time
But if you're going to Museum of Science & Industry or Garfield Park Conservatory, both of which are great, take a cab or rideshare there and back