
East Side Vacations from $179
Book a Hotel + Flight or Car together to unlock savings
Your East Side Vacation
Book a vacation package to East Side and experience the wonders of this neighborhood from dawn to dusk. From its nature and walking to its unique rhythm and vibe, there's an endless list of great reasons to visit East Side. Start your trip to East Side by checking out nearby attractions such as Calumet Park, Calumet Beach and Munson Beach. Don't just wish for it — make it a reality! Lock in your ultimate East Side vacation with Expedia and experience travel your way.
The Latest East Side Vacation Packages

Hotel Felix River North/Magnificent Mile
Reviewed on Oct 15, 2025



Waldorf Astoria Chicago
Reviewed on Oct 14, 2025

Illinois Beach Hotel
Reviewed on Oct 18, 2025
Where to stay in East Side

Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
East Side Hotel Deals

Congress Plaza Hotel
Reviewed on Oct 19, 2025

Hilton Chicago/Magnificent Mile Suites
Reviewed on Oct 19, 2025

Freehand Chicago
Reviewed on Oct 18, 2025
Discover the most popular places to visit in East Side

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do

Skydeck - Willis Tower Admission
