Great place to walk around with beautiful views of the city. Stop by next door Ohio Street Beach to see where we got engaged! Head to nearby Cupitol for coffee and a croissant sandwich.
Chicago Riverwalk
Riverwalk, Chicago, IL 60601, (877) 300-6746
One of the best ways to see the city and get some exercise. Walk the 1.25 mi path under bridges along the water. There are many restaurants and drink spots to stop at along the way.
Wendella Tours & Cruises
400 North Michigan Avenue, Chicago, IL 60611, (312) 337-1446
Great way to see the city! The tour goes through the river and then back out to the lake. The top level is open and the bottom level is an indoor bar.
Emporium Logan Square
2363 North Milwaukee Avenue, Chicago, IL 60647, (773) 697-7922
Arcade bar with decades of games, dozens of beers, pool, & 60-plus whiskeys.
Gather
4539 North Lincoln Avenue, Chicago, IL 60625, (773) 506-9300
One of Sarah's favorite spots. We've loved everything we've had here. It might be far from where you're staying but it's worth the trip!
Pequod's Pizza
2207 North Clybourn Avenue, Chicago, IL 60614, (773) 327-1512
Arguably the best pizza in Chicago. This is not your traditional deep dish.
Adler Planetarium
1300 South Lake Shore Drive, Chicago, IL 60605, (312) 922-7827
What's cooler than space? Definitely see a show if you visit. You can also walk the path around the perimeter of the building to see amazing skyline views!
The Art Institute of Chicago
111 South Michigan Avenue, Chicago, IL 60603, (312) 443-3600
Founded in 1879, The Art Institute of Chicago is one of the oldest and largest art museums in the world.
Millennium Park
201 East Randolph Street, Chicago, IL 60602, (312) 742-1168
Close to the Art Institute of Chicago, check out the "bean" aka Cloud Gate, Crown Fountain, and more!
Portillo's Hot Dogs
100 West Ontario Street, Chicago, IL 60654, (312) 587-8910
Iconic Chicago fast food! The best cheeseburger, fries, hotdog, Italian beef, and chocolate cake shake. You'll need a nap afterwards so prepare accordingly.
Big Star
1531 North Damen Avenue, Chicago, IL 60622, (773) 235-4039
Classic Chicago tex-mex spot in Wicker Park. We recommend the Al Pastor taco and margaritas!
The Second City
230 West North Avenue, Chicago, IL 60614, (312) 337-3992
Historic improv comedy theater with a variety of shows.
Beatrix
519 North Clark Street, Chicago, IL 60654, (312) 284-1377
Great spot for brunch with multiple locations around the city! Make a reservation in advance.
Yolk - Streeterville
355 East Ohio Street, Chicago, IL 60611, (312) 822-9655
Great brunch spot with multiple locations around the city! Join the waitlist before arriving from their website https://eatyolk.com/contact-locations/.
West Town Bakery & Diner
1916 West Chicago Avenue, Chicago, IL 60622, (773) 904-1414
Delicious diner style brunch spot.
Maxwell Street Depot
411 West 31st Street, Chicago, IL 60616, (312) 326-3514
One of Joe's stops while he's biking. Get a hotdog, polish sausage, or a burger.
MingHin Cuisine
2168 South Archer Avenue, Chicago, IL 60616, (312) 808-1999
Classic spot for great dim sum and hot pot in Chinatown. Take a stroll through Ping Tom Memorial Park afterwards with your bubble tea to see a great view of the river.
Promontory Point
5491 South DuSable Lake Shore Drive, Chicago, IL 60615, (312) 742-5369
Scenic park located in Hyde Park. Take a seat on the limestone blocks for a relaxing view of Lake Michigan. Walk over into Hyde Park afterwards to see the University of Chicago campus or get Steak and Eggs at Valois Diner.
Qing Xiang Yuan Dumplings
2002 South Wentworth Avenue, Chicago, IL 60616, (312) 799-1118
Chinatown spot that specializes in soup dumplings, steamed or fried, with dozens of filling options to choose from!