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

Swissotel - Chicago

21.3 km from East Side

Martha

CA $291 total

includes taxes & fees

Jul 1 - Jul 2

Omni Chicago Hotel

Streeterville, 22.2 km from East Side

Bruce

CA $269 total

includes taxes & fees

Jul 8 - Jul 9

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 23.4 km from East Side

Zhiwen

CA $207 total

includes taxes & fees

Jul 1 - Jul 2

2 restaurants; breakfast, lunch, and dinner served

LondonHouse Chicago, Curio Collection by Hilton

The Loop, 21.5 km from East Side

William

CA $440 total

includes taxes & fees

Jul 1 - Jul 2

Warwick Allerton - Chicago

Streeterville, 22.2 km from East Side

Peter Anthony

CA $238 total

includes taxes & fees

Jul 7 - Jul 8

River Hotel

The Loop, 21.5 km from East Side

Jody

CA $236 total

includes taxes & fees

Jul 5 - Jul 6

Travelodge by Wyndham Downtown Chicago

The Loop, 20.1 km from East Side

Ming

CA $207 total

includes taxes & fees

Jul 5 - Jul 6

Carleton of Oak Park

29.8 km from East Side

Barbara

CA $179 total

includes taxes & fees

Jun 29 - Jun 30

Congress Plaza Hotel

The Loop, 20.1 km from East Side

Daniel

CA $229 total

includes taxes & fees

Jun 29 - Jun 30

Freehand Chicago

River North, 22 km from East Side

Ken

CA $260 total

includes taxes & fees

Jul 5 - Jul 6

Hyatt Regency Chicago

The Loop, 21.4 km from East Side

Marianne

CA $437 total

includes taxes & fees

Jul 6 - Jul 7

Best Western Grant Park Hotel

The Loop, 19.5 km from East Side

Tammy

CA $201 total

includes taxes & fees

Jul 1 - Jul 2

The Chicago Hotel Collection - Magnificent Mile

Streeterville, 22.2 km from East Side

keary

CA $211 total

includes taxes & fees

Jun 29 - Jun 30

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 21.3 km from East Side

Jeffrey

CA $389 total

includes taxes & fees

Jun 30 - Jul 1

Hilton Chicago/Magnificent Mile Suites

Streeterville, 22.6 km from East Side

Avradita

CA $235 total

includes taxes & fees

Jul 7 - Jul 8

Silversmith Hotel Chicago Downtown

Theatre District, 20.9 km from East Side

Taylor

CA $273 total

includes taxes & fees

Jul 5 - Jul 6

Rooftop bar, alfresco dining, open daily

The Godfrey Hotel Chicago

River North, 22.4 km from East Side

Benjy

CA $282 total

includes taxes & fees

Jul 1 - Jul 2

FOUND Hotel Chicago River North

River North, 22.2 km from East Side

Nicholas

CA $201 total

includes taxes & fees

Jun 30 - Jul 1

Central Loop Hotel

Theatre District, 20.8 km from East Side

Daniel

CA $249 total

includes taxes & fees

Jul 5 - Jul 6

Club Quarters Hotel Wacker at Michigan, Chicago

The Loop, 21.5 km from East Side

George R. Bamberger

CA $256 total

includes taxes & fees

Jul 1 - Jul 2

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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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A river with a city skyline in the background, surrounded by green trees and grass.

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

River Hotel

10/10 Excellent

"Great hotel with an amazing location. Loved the purified water available on each floor along with reusable water bottles. Maid staff were excellent. Would definitely stay here again."