Paul & Sydney

Paul & Sydney

June 21, 2025 • Chicago, IL
75 Days To Go!
Paul & Sydney

Paul & Sydney

June 21, 2025 • Chicago, IL
75 Days To Go!

Things to Do

WHAT TO DO IN CHICAGO?

Shedd Aquarium

1200 S DuSable Lake Shore Dr, Chicago, IL 60605, USA
(312) 939-2438

Not only is the Shed home to 32,000 animals, but they have live marine shows that the kiddos will love. The Shed is currently the 3rd largest aquarium in the US.

Field Museum

1400 S Lake Shore Dr, Chicago, IL 60605, USA
(312) 922-9410

One of the largest museums in the world lives in Chicago! From Natural history, to ancient cultures, to the latest scientific discoveries, the Field Museum has it all.

Adler Planetarium

1300 S DuSable Lake Shore Dr, Chicago, IL 60605, USA
(312) 922-7827

Check out one of the best views of the Chicago skyline before/after you tour the museum dedicated to astronomy and astrophysics.

Millennium Park

Chicago, IL 60602, USA
(312) 742-1168

Enjoy state of the art architecture, art, concerts, exhibitions and more. Don’t forget to make a stop at the Bean, also known as “Cloudgate”!

Architectural Tour

One of the most renowned architecture tours in the United States! They typically last 1.5 hours. You will float down up and down the river while an enthusiastic guide will tell you all the inside scoop of Chicago’s historic and gorgeous architecture.

Magnificent Mile

Shop until you drop at upscale shops and fashion outlets. Start at the Chicago River and head north up to Oak Street. If you head West on Oak Street, you’ll encounter plenty of luxury stores, great if you like to window shop.

Lincoln Park Zoo

Chicago, IL 60614, USA
(312) 742-2000

Take a stroll through Chicago’s 35-acre zoo. Did we mention this one’s free? All you have to pay for is parking if you have a car.

Willis Tower

233 S Wacker Dr, Chicago, IL 60606, USA
(312) 875-0066

Formerly the Sears Tower, the newly named Willis Tower is home to the legendary Chicago sky deck. If you’re afraid of heights, you might want to sit this one out. At the sky deck, you can step “outside” the third tallest building in the Western Hemisphere. At 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck.

Bally’s Casino Chicago

600 N Wabash Ave, Chicago, IL 60611, USA
(888) 822-2559

Try your luck at the new Downtown Chicago casino!

Navy Pier

600 E Grand Ave, Chicago, IL 60611, USA
(312) 595-7437

You could set an entire day aside for this attraction! Take a ride on the Ferris Wheel (nearing 200 ft. tall!), stroll through the gardens, check out the expansive rooftop bar called Offshore, and much more. Navy Pier truly has something for everybody!

WHERE TO GRAB A DRINK & A BITE?

Cindy's Rooftop

12 S Michigan Ave, Chicago, IL 60603, USA
(312) 792-3502

Located at the top of the Chicago Athletic Association, Cindy’s has fabulous views overlooking Millennium Park. Grab a drink and enjoy!

LH Rooftop

85 E Wacker Dr 22nd Floor, Chicago, IL 60601, USA
(312) 357-1200

LondonHouse has sweeping views of the Chicago River. Both boast long lines during happy hour so be smart about your arrival time, or book a reservation in advance. It’s well worth splurging on one cocktail!

City Winery at the Riverwalk

11 E Riverwalk South, Chicago, IL 60601, USA
(312) 229-5593

City Winery is one of many spots to grab a drink on the river, this is one of our favorite things to do in the summer! Tiny Tapp and The Northman Beer & Cider Garden are also outstanding.

Bub City

435 N Clark St, Chicago, IL 60654, USA
(312) 610-4200

Country music and barbeque, what more could you need? There is always a live band around 10 PM!

Pizzeria Portofino

317 N Clark St, Chicago, IL 60654, USA
(312) 900-9018

One of our favorite spots right on the river! Known for their delicious Portofino, Italy inspired pizza, drinks and decor!

Mercadito

108 W Kinzie St, Chicago, IL 60654, USA
(312) 329-9555

Great vibes and lots of delicious Mexican options! Stop in here for a margarita and street-style tacos!

Lou Malnati's Pizzeria

439 N Wells St, Chicago, IL 60654, USA
(312) 828-9800

If you are looking for a taste of Chicago - Lou Malnati's has outstanding deep dish pizza!

Siena Tavern

51 W Kinzie St, Chicago, IL 60654, USA
(312) 471-1636

An awesome spot to grab some Italian food and a refreshing glass of wine in the summer months!

Lil' Ba-Ba-Reeba!

441 N Clark St #1, Chicago, IL 60654, USA
(312) 985-6909

Sangria and Spanish tapas! We love this little neighborhood spot right in the heart of River North!

Harry Caray's Italian Steakhouse

33 W Kinzie St, Chicago, IL 60654, USA
(312) 828-0966

This sophisticated, high energy restaurant pays tribute to Harry Caray, the beloved Chicago Cubs hall of fame sportscaster. Delicious Italian staples, steaks and seafood!