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September 2, 2022
Chicago, IL

Faye & Matthew

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    Things To Do

Things To Do

Second City? Not by our count. Chicago is world-class in so many categories—magnificent architecture, stunning museums, a foodie heaven, a beautiful water front and so much more. See below some of our favourites.

Walk Lake Shore Drive

1000 N Lake Shore Drive,

One of the prettiest strolls in the city along Lake Michigan. Start in the middle by Oak Street Beach and head north towards Lincoln Park and North Ave Beach or south towards Millennium Park and the Bean.

Millennium Park

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

Home to the Bean, Buckingham Fountain and the Pritzker Pavilion. A beautiful park next the to the Art Institute and lake front.

The Art Institute of Chicago

111 S Michigan Ave, Chicago, IL 60603

Located in downtown, one of the worlds best art museums. Right beside Millennium Park and the Buckingham fountain. Don't forget The Bean!

Oak Street Beach

IL 60611

Who needs Miami? Yes Chicago has beaches, though often crowded in the summer a great place to stop by.

Chicago Riverwalk

Riverwalk, Chicago, IL

Beautiful walk by the Chicago River with stunning architecture and plenty of restaurants and bars. If you're feeling adventurous you can rent a kayak. Or jump on a boat for an architectural tour. Either way don't fall in. And don't miss Art on the Mart at night, a huge digital projection of art onto the former merchandise market.

Cruz Blanca

904 W Randolph St, Chicago, IL 60607

Rick Bayless taco/brewery in the middle of the West Loop.

La Bouchon

1958 N Damen Ave, Chicago, IL 60647

Delicious french food in Bucktown. Cosy casual setting. Get the duck for two (trust us!)

The Loyalist

177 N Ada St, Chicago, IL

Matt's favourite burger in the city. Be sure to make a reservation. Located in the West Loop.

RL Restaurant

115 E Chicago Ave, Chicago, IL 60611

Ralph Lauren restaurant located next to their store. Highly recommend for brunch/lunch. Don't skip dessert!

Tortello

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

Faye's favourite pasta in Wicker Park. Casual counter service, spritz and wine.

Jaleo

500 N Clark, Chicago, IL 60654

Delicious Spanish tapas and cocktail concept from Jose Andres in River North. Reservation recommended.

Blue Door Kitchen & Garden

52 West Elm Street, Chicago, IL 60610
, (312) 573-4000

In the heart of the Gold Coast neighbourhood. Farm to table breakfast and brunch spot with a great patio.

Bar Mar by José Andrés

120 North Upper Wacker Drive, Chicago, IL 60606
, (312) 820-6602

Cocktail and Oyster bar. A perfect nightcap.

Trivoli Tavern

114 N Green Street, Chicago, IL 60607

A classic American tavern with great pasta. Half priced bottles of wine on Wednesdays! Also in the West Loop.

Tanta Chicago

118 West Grand Avenue, Chicago, IL 60654
, (312) 222-9700

Pisco cocktail bar with yummy Peruvian small plates. Great rooftop and happy hour in River North.

Bavette's Bar & Boeuf

218 West Kinzie Street, Chicago, IL 60654
, (312) 624-8154

Arguably the best steak in Chicago. Reserve well in advance to avoid disappointment.

bar avec

640 North LaSalle Drive, Chicago, IL 60654
, (312) 736-1740

Rooftop cocktails and small plates in River North.

Aba

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

Fantastic Mediterranean restaurant in the West Loop. Gorgeous setting, make sure you book an outdoor table!

Ramen Wasabi

2101 North Milwaukee Avenue, Chicago, IL 60647
, (773) 227-8180

Matt and Faye's favourite Sunday date night. The perfect hangover cure. Service is slow...but if Matt can handle it so can you.

Oriole

661 West Walnut Street, Chicago, IL 60661
, (312) 877-5339

Michelin star chasers this one is for you. Fine dining in the West Loop. One of the top 3 restaurants in the US. $$$

Pops For Champagne

601 N State St, Chicago, IL 60610

Champagne bar and small plates located in River North.

Mama Delia

1721 W Division Street, Chicago, IL 60622
, (312) 487-1236

Spanish Tapas in Wicker Park. Delicious small plates, sherry bar and cocktails.

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