
East Side Vacations from $266
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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

Hotel Riu Plaza Chicago
Reviewed on Feb 21, 2026

Level Chicago – Old Town
Reviewed on Feb 22, 2026

Holiday Inn Club Vacations at Lake Geneva Resort by IHG
Reviewed on Feb 19, 2026

JW Marriott Chicago
Reviewed on Feb 17, 2026

La Banque Hotel
Reviewed on Jan 26, 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

Congress Plaza Hotel
Room was very cold, key didn’t work for the side door
Reviewed on Feb 22, 2026

Hotel Riu Plaza Chicago
Great staff, clean rooms. Great location
Reviewed on Feb 21, 2026

Embassy Suites by Hilton Chicago Downtown River North
The staff were friendly, the room was clean, and this hotel is in a great location. We were able to walk to a lot of attractions. My main issue with this hotel is that it was too popular! It was really crowded when we were there and even with 4 elevators sometimes there was a wait. Still, I would ...
Reviewed on Feb 21, 2026
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

Chicago Bulls Basketball Game at United Center

Chicago River: 1.5-Hour Guided Architecture Cruise























