
East Side Vacations from $235
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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

The Royal Sonesta Chicago River North
Reviewed on Dec 27, 2025

Trump International Hotel & Tower Chicago
Reviewed on Dec 27, 2025

Hotel Riu Plaza Chicago
Reviewed on Dec 27, 2025

Pendry Chicago
Reviewed on Dec 27, 2025

Level Chicago – Old Town
Reviewed on Dec 25, 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

Hilton Chicago/Magnificent Mile Suites
Hospitality is amazing! Very gracious and courteous
Reviewed on Dec 27, 2025

Palmer House a Hilton Hotel
Excellent stay, we loved it
Reviewed on Dec 27, 2025

Club Quarters Hotel Wacker at Michigan, Chicago
Friendly and knowledgeable employees who will go out of their way to assist guests. Clean and quiet rooms even though it's located in the heart of Chicago.
Reviewed on Dec 26, 2025
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

Chicago Bulls Basketball Game at United Center
























