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June 18, 2022
Chicago, Illinois

Olivia & Ryan

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Things To Do

The Violet Hour

1520 North Damen Avenue, Chicago, IL 60622
, (773) 252-1500

One of our favorite cocktail bars in the city, and where we had one of our first dates.

The Art Institute of Chicago

111 South Michigan Avenue, Chicago, IL 60603
, (312) 443-3600

One of our favorite spots to get lost in the city.

Tortello

1746 West Division Street, Chicago, IL 60622
, (773) 360-1293

Best pasta in Chicago. Period.

Lost Larson

2140 West Division Street, Chicago, IL 60622
, (773) 770-9015

One of our favorite spots to grab coffee and pastries. Grab a slice of Princess Cake-- they deliver, too!

The Northman Beer & Cider Garden

233 E. Riverwalk, Chicago, IL 60601
, (773) 382-6165

One of our favorite spots to grab European-inspired food and cider. Perfect for a warm summer night or a casual afternoon break.

Frontera Grill

445 North Clark Street, Chicago, IL 60654
, (312) 661-1434

Where we met for the first time and had our first date!

SPACE 519

200 East Chestnut Street, Chicago, IL 60611
, (312) 751-1519

Awesome brunch/lunch spot with a boutique/concept store inside. Right off of the hustle and bustle of Michigan Ave, and not far from the lakefront.

Kumiko

630 West Lake Street, Chicago, IL 60661
, (312) 285-2912

Our favorite cocktail bar in the city-- perfect for sake, cocktails, mocktails, and small Japanese-inspired bites.

Le Bouchon

1958 North Damen Avenue, Chicago, IL 60647
, (773) 862-6600

We've had many a bottle of wine here. Amazing French food-- and you'll feel like you're at a small bistro in France. It's super authentic.

Obelix

700 North Sedgwick Street, Chicago, IL 60654
, (312) 877-5348

One of our favorite new restaurants, opened by the owners of Le Bouchon. Reservations open on 5/5/2022-- great French food, awesome ambiance: you can't miss it.

North Pond Nature Sanctuary

North Lincoln Park West, Chicago, IL 60614

One of the prettiest places to walk (and eat!) in the city

Jeni's Splendid Ice Creams

908 West Randolph Street, Chicago, IL 60607
, (708) 540-6124

You know you have to!

Molly's Cupcakes

2536 North Clark Street, Chicago, IL 60614
, (773) 883-7220

There's a location in Streeterville on Illinois St too! These are some of our favorite cupcakes to share when we're hosting dinners at our apartment.

mfk. restaurant

432 West Diversey Parkway, Chicago, IL 60614
, (773) 857-2540

One of our favorite restaurants in the city-- a cozy neighborhood spot that specializes in Spanish food.

The Glunz Tavern

1202 North Wells Street, Chicago, IL 60610
, (312) 642-3001

Oldest wine shop owned by the same family in the USA. For our fellow wine-nerds :) (and an awesome place to grab some tavern food!)

Off Color Brewing Taproom The Mousetrap

1460 North Kingsbury Street, Chicago, IL 60642
, (312) 929-2916

Our favorite beer spot in the city

Cindy's Rooftop

12 South Michigan Avenue, Chicago, IL 60603
, (312) 792-3502

Great rooftop bar!

Printers Row Wine Bar and Shop

719 South Dearborn Street, Chicago, IL 60605
, (312) 663-9314

Great little hole-in-the-wall for a glass of wine

Bar Sótano

443 North Clark Street, Chicago, IL 60654
, (312) 391-5857

LOVE the cocktails here-- awesome Mexican food!

XOCO

449 North Clark Street, Chicago, IL 60654
, (312) 723-2131

Next door to Frontera and Bar Sotano, awesome place for casual Mexican food.

Sawada Coffee

112 North Green Street, Chicago, IL 60607
, (312) 344-1750

Awesome coffee/matcha spot in the West Loop

Roister Restaurant

951 West Fulton Market, Chicago, IL 60607

Get the buttermilk fried chicken, it will change your life. Reservations in advance highly recommended!

Billy Goat Tavern (The Original)

Michigan Avenue, Chicago, IL 60611
, (312) 222-1525

A Chicago classic, hole-in-the-wall

Superdawg Drive-In

6363 North Milwaukee Avenue, Chicago, IL 60646
, (773) 763-0660

This needs no introduction.

Galit

2429 North Lincoln Avenue, Chicago, IL 60614
, (773) 360-8755

Amazing Israeli food-- from the same owners of Shaya in New Orleans (one of our favorites)

For all the days along the way
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