Things To Do

Activities

Architectural Boat Tour

Bundle up and learn everything there is to know about the buildings that make Chicago America’s most beautiful skyline. Tours are 45 or 90 minutes and get busy, even in the late fall. Book ahead online through Wendella Boats ("Chicago River Architectural Tour") (wendellaboats.com).

Chicago River Walk

The south bank of the Chicago River has a beautiful walking path and several bars, restaurants, and food and souvenir stalls, for those who want to take in the beauty of downtown Chicago without getting in a boat.

The Art Institute of Chicago

We have spent many many hours perusing the galleries of the Art Institute. Get lost among Hoppers, O’Keefes, and Monets in the Midwest!

Museum of Contemporary Art Chicago

If modern is more your style . . .

There's Always Shopping...

There’s always time for shopping around Michigan Avenue and Rush Street between Erie Street and Oak Street.

Millennium Park and the Bean

You’ve seen it in pictures, and maybe you’ve even seen the imposter under the apartment building in Tribeca, but there is nothing like the Bean in person and the beautiful views from Millennium Park.

Lincoln Park/Armitage Ave.

An iconic neighborhood and street adorned with cute stores, coffee shops, and some of the city’s most beloved bars and restaurants.

The West Loop

Our old neighborhood has many of Chicago’s best and hottest restaurants and bars, along with some shopping!

Food

A trip to Chicago isn’t complete without some obligatory food stops. Here is our shortlist:

Italian Beef

During our year in Chicago, we went on an Italian beef tour, vowing to try every place that makes a beef in the city. Sweet or hot—we’ll let you decide. Mr. Beef, Portillo’s, and Al’s are at the top of our list.

Chicago-Style Pizza

Yes, Chicago is known for deep dish. It’s not your average dollar slice. Check out Lou Malnati’s, Giordano’s or Gino’s East, if you want a taste for yourself. But the thin crust at Lou’s is also great—we order it with spinach and tomato. Or for Chicago’s other classic, tavern style, check out Zarella. Don’t forget the hot honey and book ASAP.

Burgers

Au Cheval (put your name down early and prepare to wait), Momotaro, the Izakaya (an Asian twist), The Loyalist (moody, but a classic).

Italian

Monteverde (our favorite restaurant in Chicago, email reservations@monteverdechicago.com ASAP and include “Gottstein-Schaefer Wedding-Reservation Request” in the subject line, burrata buns are a MUST), Topo Gigio (red sauce Italian, great espresso martini).

Steak

A sport in Chicago. Gibson’s (nothing like it, pie slices are good for four), Maple & Ash (a party), Joe’s (people think stone crab, but the steak is a sleeper), Gene & Georgetti (old school), Bavette’s (Chicago’s 4 Charles. Shoot your shot for a res, may the odds be ever in your favor).

Sushi

Sushi Dokku, Sushi San, Miru, all different; all good.

Great Food and a Great Vibe

Gilt Bar, Trivoli Tavern, Erie Cafe, Rose Mary, Aba, Green Street Smoked Meats, Le Colonial, Lux Bar, Wiener Circle (“great” is stretch, more for the memories, cheese fries…open until 4am on the weekends)

Breakfast, Brunch, Lunch

Tempo (a Gottstein family staple), Doc B’s, RL Restaurant, Doma, Eleven City Diner, Publican Quality Meats, Good Ambler, Hendrickx Bakery (tucked away, great croissants)

Coffee

Some nearby options: Intelligentsia, Big Shoulders, Goddess and the Baker; Some further away ones: Sawada (if you’re a matcha lover, worth the trek!), Starbucks Reserve, Ralph’s

Bars

Lazy Bird, Fox Bar, The Office, or throw a frozen shot glass at the bell at Federales (a Sam classic).