When is the best time to go to East Side?

The best time to visit East Side, Illinois is typically during the late spring (May to early June) or early autumn (September to October) when the weather is most pleasant. During these months, you'll find comfortable temperatures, generally ranging from 15°C to 25°C, which are ideal for exploring the area's outdoor attractions and enjoying local events without the extreme heat of summer or the chill of winter. The foliage in autumn can be quite lovely, adding to the scenic appeal. For those interested in outdoor activities like hiking or cycling along the Mississippi River, these seasons offer the most agreeable conditions.

Can I cancel my hotel reservation on Expedia?

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel’s cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right East Side hotel for you.

How can I save on a East Side hotel booking with Expedia?

With Expedia, you’ll unlock our lowest prices by becoming a member. It’s free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on East Side hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.

How much is the nightly rate at a East Side hotel?

Hotel prices in East Side often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

10 Best Hotels in East Side, Chicago for 2026

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Our top choices for East Side hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 21.3 km from East Side

Gina

CA $458 total

includes taxes & fees

Jun 14 - Jun 15

Congress Plaza Hotel

The Loop, 20.1 km from East Side

Jennifer

CA $222 total

includes taxes & fees

May 27 - May 28

The Chicago Hotel Collection - Magnificent Mile

Streeterville, 22.2 km from East Side

Ontario

CA $312 total

includes taxes & fees

Jun 3 - Jun 4

Freehand Chicago

River North, 22 km from East Side

Michael

CA $316 total

includes taxes & fees

Jun 10 - Jun 11

Travelodge by Wyndham Downtown Chicago

The Loop, 20.1 km from East Side

Amber

CA $176 total

includes taxes & fees

May 27 - May 28

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 23.4 km from East Side

Robin

CA $257 total

includes taxes & fees

Jun 22 - Jun 23

Club Quarters Hotel, Central Loop, Chicago

Theatre District, 20.8 km from East Side

Mary

CA $190 total

includes taxes & fees

May 27 - May 28

Silversmith Hotel Chicago Downtown

Theatre District, 20.9 km from East Side

Brittany

CA $369 total

includes taxes & fees

Jun 21 - Jun 22

Eurostars Magnificent Mile

River North, 22.2 km from East Side

Belinda

CA $263 total

includes taxes & fees

May 27 - May 28

The Wade

Streeterville, 21.8 km from East Side

Molly

CA $348 total

includes taxes & fees

May 27 - May 28

Best Western Grant Park Hotel

The Loop, 19.5 km from East Side

cheri

CA $224 total

includes taxes & fees

May 27 - May 28

Hotel Riu Plaza Chicago

Streeterville, 22 km from East Side

sierra

CA $287 total

includes taxes & fees

May 27 - May 28

Hilton Chicago

The Loop, 19.9 km from East Side

Robert

CA $367 total

includes taxes & fees

May 27 - May 28

Staypineapple, An Iconic Hotel, The Loop

Theatre District, 21.1 km from East Side

Brenda

CA $417 total

includes taxes & fees

May 27 - May 28

River Hotel

The Loop, 21.5 km from East Side

Jaden

CA $310 total

includes taxes & fees

May 27 - May 28

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Streeterville, 22 km from East Side

Nicholas

CA $261 total

includes taxes & fees

May 27 - May 28

Central Loop Hotel

Theatre District, 20.8 km from East Side

Tasha

CA $212 total

includes taxes & fees

May 27 - May 28

Warwick Allerton - Chicago

Streeterville, 22.2 km from East Side

Natalia

CA $257 total

includes taxes & fees

May 27 - May 28

Hotel Felix River North/Magnificent Mile

River North, 22.4 km from East Side

Rodolfo

CA $203 total

includes taxes & fees

May 27 - May 28

Millennium Hotel Knickerbocker Chicago

Streeterville, 22.6 km from East Side

Eileen

CA $269 total

includes taxes & fees

May 27 - May 28

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Where to stay in East Side

Find the best East Side areas and neighborhoods for the activities you enjoy most. Learn more about 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.

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Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

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The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Top East Side Hotel Reviews

Hilton Chicago

10/10 Excellent

"Great experience!"

Hotel Riu Plaza Chicago

10/10 Excellent

"This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment! The rooftop bar was very pleasant place to sit and chill. Strongly recommended!!!"

Club Quarters Hotel, Central Loop, Chicago

8/10 Good

"Convenient location for travellers. Rooms are quite old and the housekeeping is not very good because we found some leftover food in the closet when we checked in and had to change to another room. Also all the coffee cups in our room are not cleaned… I mean you can see the stains in the photo"

Aloft by Marriott Chicago Mag Mile

6/10 Okay

"The room was ok. There were no bags on the trash can, no microwave. The breakfast was not what I expect it to be. You have to order on line then you pick up. It was not a buffet where you get to pick as much food as you want and sit down to eat like other hotels. The pool was so small that you could barely do anything if people were there and the water was so cold. The only thing nice I could say is that the staff was great and very helpful."

Fairmont Chicago at Millennium Park

8/10 Good

"Stayed here for a recent trip to Chicago and overall the experience was okay. The location is convenient for downtown attractions and Millennium Park, and the hotel itself was clean and comfortable. Staff were generally polite and check-in was fairly smooth. The rooms were decent, though some areas felt a little dated for the price. Amenities and service were fine but nothing especially memorable. It worked well as a place to stay while exploring the city, but I expected a bit more considering the reputation and cost. Good option if location is your priority, but not necessarily a standout luxury experience."

The Chicago Hotel Collection Ambassador Gold Coast

2/10 Terrible

"Terrible hotel, when I made the reservation they told me I had free breakfast but they charged me $70 extra for it, very dirty carpet, loud AC, no water in the room even though I was trying to pay so I had to go down lobby at 3am to get water, over all one of the horrible hotel I stayed 👎👎"

Hotels in East Side, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Our top choices for East Side hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Congress Plaza Hotel

The Chicago Hotel Collection - Magnificent Mile

Freehand Chicago

Travelodge by Wyndham Downtown Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Club Quarters Hotel, Central Loop, Chicago

Silversmith Hotel Chicago Downtown

Eurostars Magnificent Mile

The Wade

Best Western Grant Park Hotel

Hotel Riu Plaza Chicago

Hilton Chicago

Staypineapple, An Iconic Hotel, The Loop

River Hotel

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Central Loop Hotel

Warwick Allerton - Chicago

Hotel Felix River North/Magnificent Mile

Millennium Hotel Knickerbocker Chicago

Where to stay in East Side

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top East Side Hotel Reviews

Hilton Chicago

Frequently asked questions

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