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A & B

A guide for guests

No. 03

Our Chicago

A few of our favorite places in Chicago, for anyone who has a little extra time to explore.

Loose pen sketch of the Chicago skyline from the lakefront: Willis Tower, the Hancock, a raised river bridge, an L train, and people walking a beagle and a dachshund along the path

01 / 04

Eat

Restaurants & cafés

  • Il Milanese

    Lincoln Square

    Our favorite restaurant in Chicago. Excellent pasta, good wine, and the kind of place we happily go back to again and again.

  • Le Colonial

    Gold Coast

    Beautiful interiors, French-Vietnamese food, and an excellent excuse to dress up a little for dinner.

  • Old Pueblo

    Lincoln Park

    Sonoran-inspired Mexican food, homemade tortillas, and margaritas. We'd recommend making time for the guacamole, too.

02 / 04

Drink

Bars & wine

  • King of Cups

    Lincoln Park

    Where we went on our first date and returned to celebrate our engagement. Moody, a little theatrical, and home to some excellent cocktails. Clearly, we're sentimental about this one.

  • Cindy's Rooftop

    The Loop

    Come for a cocktail, stay for the views. Millennium Park, Lake Michigan, and a pretty spectacular look at Chicago.

03 / 04

Explore

Architecture, art & the lake

  • Chicago Architecture Boat Tour

    Chicago River / Downtown

    Brandon's an architect, so naturally this one makes the list. The best way to see the city, learn a little history, and appreciate why Chicago's architecture is so special.

  • Obama Presidential Center

    Woodlawn / Jackson Park

    A new addition to Chicago's South Side, with a museum, art, architecture, and plenty to explore. Worth making the trip south. We recommend buying museum tickets in advance.

  • Art Institute of Chicago

    The Loop

    One of our favorite ways to spend an afternoon downtown. Come for the art, stay longer than you planned.

04 / 04

Around the Neighborhood

Henry + Oscar's Walking Route

  • Coffee Lab & Roasters

    Lakeview

    Really good coffee, creative lattes, and a perfect place to start the morning before wandering the neighborhood.

  • Vaughan's Pub

    Lakeview

    A proper neighborhood Irish pub. Nothing fancy, just cold drinks, a good crowd, and somewhere you'll want to settle in.

  • Farm Bar

    Lakeview

    Comfort food, good drinks, and an easygoing neighborhood atmosphere. Just the kind of place we love having nearby.