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August 6, 2022
Chicago, IL

Madi & Duke

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    Things To Do

Things To Do

Some of our favorite things to do in the city along with some of our top places to eat and drink! We highly recommend booking reservations well in advance for Chicago restaurants.
Chicago Architecture Boat Tour

Chicago Architecture Boat Tour

401 N Michigan Avenue, Chicago, IL 60611
, (312) 222-9328

The best way to see Chicago- from the water! Duke and I love this architecture tour. Grab a drink, sit on the deck, and enjoy the beautiful city from the river.

Michigan Avenue Shopping

Michigan Avenue Shopping

Michigan Avenue, Chicago, IL

Walking up and down world famous Michigan Avenue is the best way to get some shopping in!

Navy Pier

Navy Pier

600 East Grand Avenue, Chicago, IL 60611
, (312) 595-7437

Navy Pier is located right off of Lake Michigan and has wonderful restaurants and great spots to grab drinks!

Lakefront Trail

Lakefront Trail

Lakefront Trail, Chicago, IL

Chicago's lakefront trail is easily accessible from the city and a great way to enjoy Lake Michigan! Walk miles up and down the coast.

Chicago Riverwalk

Chicago Riverwalk

Riverwalk, Chicago, IL 60601
, (877) 300-6746

The Riverwalk has incredible breweries and restaurants and is a great place to walk on the water right in the heart of the city!

Wrigley Field

Wrigley Field

1060 West Addison Street, Chicago, IL 60613
, (773) 404-2827

Grab a Chicago dog and a beer and catch a game at the historical Wrigley Field!

Goose Island Brewhouse

Goose Island Brewhouse

1800 North Clybourn Avenue, Chicago, IL 60614
, (312) 915-0071

Visit the brewery where they make our favorite beer, Goose Island!

Millennium Park

Millennium Park

201 East Randolph Street, Chicago, IL 60602
, (312) 742-1168

A park in the heart of the city where you can see the infamous bean! (We're still not sure what the hype is about... but see for yourself!)

Aba

302 North Green Street, Chicago, IL 60607
, (773) 645-1400

Mediterranean restaurant with a rooftop that has great city views.

Naveen's Cuisine

2523 West North Avenue, Chicago, IL 60647
, (773) 230-9320

Go enjoy wine and cooking with this AWESOME cooking class at Naveens!

Three Dots and a Dash

435 North Clark Street, Chicago, IL 60654
, (312) 610-4220

Madi's favorite bar! This underground tiki bar in the city is a must-visit that has great bites and fun tiki cocktails.

Gibsons Bar & Steakhouse

1028 North Rush Street, Chicago, IL 60611
, (312) 266-8999

Great steakhouse for cocktails and dinner!

Maple & Ash

8 West Maple Street, Chicago, IL 60610
, (312) 944-8888

Madi and Duke's favorite steakhouse in Chicago!

Sapori Trattoria

2701 North Halsted Street, Chicago, IL 60614
, (773) 832-9999

Italian restaurant just north of downtown in the famous Lincoln Park!

Cindy's Rooftop

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

Grab drinks at this rooftop with great city views on the lake!

LondonHouse Chicago

85 East Wacker Drive, Chicago, IL 60601
, (312) 357-1200

Where Duke proposed to Madi! Go to this hotel rooftop bar for incredible river and skyline views.

Pizzeria Portofino

317 North Clark Street, Chicago, IL 60654
, (312) 900-9018

A cute, tuscan pizza spot on the river!

RPM Seafood

317 North Clark Street, Chicago, IL 60654
, (312) 900-9035

Grab some great food on the river at this seafood restaurant!

The Darling

905 West Randolph Street, Chicago, IL 60607
, (312) 285-2609

Another one of Madi's favorite cocktail bars in the city! If you can - book a table in the library!

Rose Mary

932 West Fulton Street, Chicago, IL 60607
, (872) 260-3921

Grab croatian fusion at this hot spot!

Happy Camper Pizzeria

1209 North Wells Street, Chicago, IL 60610
, (312) 344-1634

A fun, hip pizza joint with cook drinks and great pizza!

Little Goat Diner

820 West Randolph Street, Chicago, IL 60607
, (312) 888-3455

Amazing breakfast!

Alla Vita

564 West Randolph Street, Chicago, IL 60661
, (312) 667-0104

An Italian restaurant with amazing pizza and pasta, of course!

Utopian Tailgate

1608 North Wells Street, Chicago, IL 60610
, (312) 210-7799

For our party crowd, an awesome rooftop with drinks and music!

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