Chicago Vacation Ideas

Have fun in the "Windy City"! So much to choose from, where do you start? Here are some ideas.

Year Round Vacation Ideas in Chicago

The Sears Tower Skydeck, 233 So. Wacker Drive, open year round, offers visitors breathtaking views from the world's tallest building. A big tourist attraction so expect crowds and long waits.

The Hancock Observatory, another great place to view the city. 875 N. Michigan Avenue. While you're there, stop in at The Signature Room on the 95th floor for fine dining with fantastic views.

Want to do some shopping? Head out to The Shops @ North Bridge for some of the finest department stores, Gurnee Mills with over 200 manufacturers and retail outlets stores, the Water Tower Place for premier shopping at the Magnificent Mile. Just a few to get you started.

Many museums and galleries to choose from. When you get hungry, you can choose from a tasty hotdog or pizza at stands throughout the city or opt for fine dining in the fancier restaurants and hotels.

Lots to see at the Field Museum on So. Lake Shore Drive. Nine acres of floor space with educational exhibitions both permanent and temporary. Call for information on discounted and free days. 312-922-9410.

Enjoy some free fun at the Lincoln Park Zoo on North Clark Street, open year round. Holiday season offers a Zoolights display. Call 312-742-2000.

Close to the Lincoln Park Zoo, you can relax and unwind at the Lincoln Park Conservatory. Stroll through the 4 display houses of tropical palms and ferns in a peaceful setting of greenery. Open year round and free. 2391 North Stockton Drive. 312-742-7736.

Shedd Aquarium, 1200 So. Lake Shore Drive, is the world's largest indoor aquarium.

Spring Vacation Ideas in Chicago

If you're visiting in March, don't miss The BELGARD Chicago Flower and Garden Show

Great reviews for Wendella's Boat Tours, 7 days a week from April through November. For a fun day on the water, try the architectural tours, sightseeing, wine tasting tours, summer fireworks cruises or ask about the Chicago Water Taxi with their reasonable rates of $2 a ride between Chinatown and the Magnificent Mile. Call 312-337-1446 for directions and hours of operation.

You can also expect easy and inexpensive travel throughout the city via buses, subways, and elevated trains at reasonable prices.

Sports enthusiasts will enjoy:

  • Harness Racing at Maywood Park Race Track just 10 miles south of O'Hare, 708-343-4800
  • The Chicagoland Speedway in nearby Joliet, 815-727-RACE
  • Wrigley Field, home to the Chicago Cubs, at W. Addison Street, 866-652-2827

Call for further information for events throughout the year.

Summer Vacation Ideas in Chicago

Find out more about A Taste of Chicago's food festival in Grant Park on our June Vacation Ideas page. Aside from festivals, Grant Park also sponsors free concerts, classes, and outdoor movies.

Stroll along Chicago's lakefront trail near Oak Street Beach for a great view of Lake Michigan and the skyline.

Read more about Chicago's Annual Blues Festival in June.

Winter Vacation Ideas in Chicago

Visit our New Year's Eve Parties page to see what's happening at Navy Pier.

Bring the family to Millennium Park for some ice skating fun.

Did You Know?

You can visit transitChicago.com for bus and rail transport information for all your needs when traveling in Chicago.

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