
East Side Holidays
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Your East Side Holiday
Book a holiday package to East Side and experience the wonders of this neighbourhood 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 holiday with Expedia and experience travel your way.
Our guide on 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.
Our pick of the best East Side Hotel Deals

Congress Plaza Hotel
"Hotel is pretty "okay" if you are going for business, but our experience was not nice. The Air Conditioner wasn't working on a 65-80 degree outside, I told the front desk if they can help or make a room change but the solution was to give me a floor fan, not the type of help I was hoping and did ..."
Reviewed on 27 May 2026

Hotel Riu Plaza Chicago
"Location is perfect. And rooftop bar & view is amazing"
Reviewed on 28 May 2026

The Chicago Hotel Collection - Magnificent Mile
"I had travel delays and a situation with my husband and my luggage and they have been very nice about it . Front desk staff is very kind and professional"
Reviewed on 27 May 2026
Frequently asked questions
Discover the most popular places to visit in East Side

Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
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