East Side Vacations from $403
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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
Hotel Riu Plaza Chicago
Reviewed on Jan 25, 2026
Level Chicago – Old Town
Reviewed on Jan 18, 2026
LondonHouse Chicago, Curio Collection by Hilton
Reviewed on Jan 25, 2026
Trump International Hotel & Tower Chicago
Reviewed on Jan 24, 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 clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ...
Reviewed on Jan 20, 2026
Embassy Suites by Hilton Chicago Downtown River North
This was a really nice place to stay, especially for the pricce! It’s located in a great location in downtown Chicago close to many restaurants, shops, and grocery stores, museums and public transportation!There are some wonderful cafés to visit right outside the hotel, including a French cafe, and ...
Reviewed on Jan 24, 2026
Hotel Riu Plaza Chicago
Incredible location and wonderful satff
Reviewed on Jan 23, 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
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Ticket
