May 6, 2023

Chicago, IL

Chicago Guide

Chicago is always changing and evolving which is what makes it exciting (fun fact: it has 77 distinct neighborhoods!). It's a city that brings us so much happiness, and we are so excited to spend the weekend with you in our favorite place! Whether you are going to a museum, walking by the lake, or trying a new restaurant, there are new discoveries and beauty everywhere-- and we can't wait for you to explore. Here are some of our favorite places.

The Art Institute of Chicago

111 South Michigan Avenue, Chicago, IL 60603

The museum hosts approximately 1.5 million people annually!

Lincoln Park

2001 N Clark St, Chicago, IL 60614, Chicago, IL 60611

Not to be confused with the band. Incredible farmer's market on Saturdays.

Chicago Cubs Game

1060 West Addison Street, Chicago, IL 60613

Personally, we think the food is better at the White Sox Stadium, but they are out of town.

Chicago Architecture River Boat Tour

400 Michigan Avenue, Chicago, IL 60611

Best views of the city!

Garfield Park Conservatory

300 North Central Park Avenue, Chicago, IL 60624

One of the largest and most stunning botanical conservatories in the nation.

Millennium Park

201 East Randolph Street, Chicago, IL 60601

#MirrorPic at The Bean.

Barry's River North

11 West Erie Street, Chicago, IL 60654

Take a class with Holly, Joe, or Kate.

The California Clipper

1002 North California Avenue, Chicago, IL 60622

Circa-1937 bar with a revamped yet still retro space & a huge list of old-fashioned cocktails.

Old Town Ale House

219 West North Avenue, Chicago, IL 60610

Laid-back dive bar near Second City with a storied past, old-school jukebox & funky art. One of Anthony Bourdain's favorites.

LH Rooftop

85 East Wacker Drive, Chicago, IL 60601

A must for out of towners.

The Up Room at Cafe Robey

2018 West North Avenue, Chicago, IL 60647

Our favorite view in the entire city.

Cindy's Rooftop

12 South Michigan Avenue, Chicago, IL 60603

Order the Prickly Pear.

Cole's Bar

2338 North Milwaukee Avenue, Chicago, IL 60647

Lia's favorite bar in her favorite neighborhood: Logan Square.

Sluggers World Class Sports Bar and Grill & Dueling Pianos

3540 North Clark Street, Chicago, IL 60657

John's favorite bar. Get in the batting cage.

Avec

615 West Randolph Street, Chicago, IL 60661

BRUNCH and bottomless mimosas. Order the bacon wrapped dates and thank us later.

Mindy's Bakery

1623 North Milwaukee Avenue, Chicago, IL 60647

Explore Wicker Park neighborhood after for shopping and drinking.

EZ Inn

921 North Western Avenue, Chicago, IL 60622

Order a Chicago Handshake if you're real.

The Green Mill

4802 North Broadway, Chicago, IL 60640

Catch a late night jazz session and see Al Capone's old booth.

Giant

3209 West Armitage Avenue, Chicago, IL 60647

Lia's favorite restaurant.

Bavette's

218 West Kinzie Street, Chicago, IL 60654

John's favorite restaurant.

Pequod's Pizza

2207 North Clybourn Avenue, Chicago, IL 60614

The best deep dish in the city.

Galit

2429 North Lincoln Avenue, Chicago, IL 60614

Was just awarded their first Michelin Star. Lia's second favorite restaurant.

Chicago Bagel Authority

953 West Armitage Avenue, Chicago, IL 60614

The ultimate hangover cure.

Little Goat Diner

820 West Randolph Street, Chicago, IL 60607

Best breakfast in the city. Worth exploring the West Loop after.

For all the days along the way

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L & J

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