
East Side Vacations from $263
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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


La Banque Hotel
Reviewed on Nov 30, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Reviewed on Dec 18, 2025

Waldorf Astoria Chicago
Reviewed on Jan 5, 2026

Hotel Riu Plaza Chicago
Reviewed on Jan 9, 2026
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

Hilton Chicago/Magnificent Mile Suites
We had a wonderful stay at the Hilton. The staff was exceptionally helpful in providing any information we neede. A shout out to Latis and Christian, who were extremely friendly, always created us with a smile and we’re eager to help. We will definitely stay here again.
Reviewed on Jan 6, 2026

Hilton Chicago
The hotel property was amazing! Numerous options for dining and relaxing. The room was clean and inviting.
Reviewed on Jan 8, 2026

Palmer House a Hilton Hotel
Room was very clean and staff was great
Reviewed on Jan 6, 2026
Discover the most popular places to visit in East Side

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.

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

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

Skydeck - Willis Tower Admission

Chicago Bulls Basketball Game at United Center























