Grant Park is where you want to head first because it is home to the Shedd Aquarium, the Adler Planetarium, the Field Museum and the Art Institute. Also check out Maggie Daley Park which is directly adjacent to Grant park and has activities for kids of all ages. Located in the center of Grant Park is the beautiful Buckingham Fountain!
I recommend the City Pass for seeing attractions while saving money!
It includes the following:
The Art Institute of Chicago
Museum of Science and Industry
Adler Planetarium Skydeck Chicago at Willis Tower and/or the 94th floor of the John Hancock Center, 360 CHICAGO (We like the latter location because there is a Cheesecake factory there, but the Willis Tower is taller)
A fun way to get around and see awesome stuff is booking a Segway tour. It’s quite an experience if you haven’t ridden one before!
Navy Pier has something going on all times of the year. We have especially enjoyed the July 4th Fireworks, the rooftop dining, listening to live music, and attending the Winter Wonderfest.
See a show or watch a concert at any one of Chicago’s amazing theaters or performance venues! Visit Millennium Park and take your selfie with the iconic Cloud Gate . Don’t leave before being awed by the Crown Fountain – sit awhile and watch it!
Stop into the Chicago Cultural Center (It’s free!) and always interesting!
Take a walk along the lake or cross over the Michigan Avenue Bridge, look up to see the Tribune Tower (stop into the lobby and read the walls) . While on your walk, check out (my favorite artist!) Chagall’s Four Seasons mural near the Chase Tower Plaza, at 10 South Dearborn Street. The underground Chicago Pedway is a great way to get around when the weather is freezing! Go Shopping or watch a parade along the The Magnificent Mile (especially at Christmas time!)
In Winter, its worth the drive a little way out of the city to see Chicagoland’s gardens lit up for the holidays. You can see this at the Chicago Botanical Gardens or the Morten Arberetum .
On warm days, head to the beach! Here is a list of the best Chicago beaches and bike along the Lakefront Trail, or you can head north a bit and try out Illinois Beach State Park for some picnicking, beach bumming and summertime fun!
For architecture lovers, many people love the Chicago Architecture River Cruise to introduce them to the city.
For more architecture and fans of Frank Lloyd Wright, please visit Robie House.
Chicago Odyssey Dinner Cruise will also give you great views of the city buildings.
Take a step back in time by entering the Palmer House Hilton Historic Lobby and take a look around, or take a tour of the Glessner House Museum and be transported back to the 1800’s.
Catch a Chicago Cubs Game at Wrigley Field.
Enjoy the Lincoln Park Zoo ! It’s FREE!
Another free attraction is the Money Museum at the Federal Reserve Bank
Don’t miss the Garfield Park Conservatory (also free!)
For more culture, there is lots to see and experience in Chicago’s Chinatown. You can take a tour of the area. Our go to places to eat are the Triple Crown and Legend Tasty House for a rolled ice-cream treat!
Places to Eat:
Cheaper: Next to the Historic Chicago Water Tower is the Water Tower Shopping Center, where you will find a variety of wonderful food eateries. It’s also fun to check out the Lego store in Water Tower Place.
Most fun: Be a spy at the SafeHouse restaurant or find a place to eat along the Chicago Riverwalk in the summer. Tradition: We love to eat at Maggiano’s downtown for Thanksgiving and get Chicago deep dish Giordanno’s Pizza the next day!
Expensive and amazing strange (but worth it!): Alinea
First place: Lollapalooza (Mostly teens and twenties, but I saw every age in attendance!) Along with bragging rights you get an experience of a lifetime!
Second place: Chicago Air and Water Show. Have Fun!