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?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in East Side.

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

Members always get our best prices. Find our best East Side hotel deals by joining Expedia’s free travel rewards program today. As a member, you can unlock instant savings and member perks when you’re logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in 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.

The Best Hotels in East Side, Chicago - 2026 Updated Prices

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Our top choices for East Side hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 13.2 mi from East Side

Julie

includes taxes & fees

9 Aug - 10 Aug

Travelodge by Wyndham Downtown Chicago

The Loop, 12.5 mi from East Side

Marobe

includes taxes & fees

10 Aug - 11 Aug

Freehand Chicago

River North, 13.7 mi from East Side

Clifton

includes taxes & fees

10 Aug - 11 Aug

FOUND Hotels, Chicago, Series by Marriott

River North, 13.8 mi from East Side

Lia

includes taxes & fees

26 Jul - 27 Jul

Superior Apartment, 2 Bedrooms, Kitchen | Living area | LED TV, Netflix, Hulu, streaming services

LIVN - West Loop Chicago

13 mi from East Side

Pedro

includes taxes & fees

19 Jul - 20 Jul

Congress Plaza Hotel

The Loop, 12.5 mi from East Side

Tammy C

includes taxes & fees

10 Aug - 11 Aug

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 14.6 mi from East Side

Tina

includes taxes & fees

27 Jul - 28 Jul

Silversmith Hotel Chicago Downtown

Theatre District, 13 mi from East Side

Donilyn

includes taxes & fees

9 Aug - 10 Aug

Palmer House a Hilton Hotel

Theatre District, 12.9 mi from East Side

Britney Q

includes taxes & fees

9 Aug - 10 Aug

The Chicago Hotel Collection - Magnificent Mile

Streeterville, 13.8 mi from East Side

Precious

includes taxes & fees

27 Jul - 28 Jul

The Wade

Streeterville, 13.6 mi from East Side

Richard

includes taxes & fees

9 Aug - 10 Aug

Warwick Allerton - Chicago

Streeterville, 13.8 mi from East Side

Peter Anthony

includes taxes & fees

13 Aug - 14 Aug

Best Western Grant Park Hotel

The Loop, 12.1 mi from East Side

Tammy

includes taxes & fees

9 Aug - 10 Aug

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Loop, 12.6 mi from East Side

Dean

includes taxes & fees

9 Aug - 10 Aug

Staypineapple, An Iconic Hotel, The Loop

Theatre District, 13.1 mi from East Side

Zoe

includes taxes & fees

9 Aug - 10 Aug

Hilton Garden Inn Chicago Downtown South Loop

The Loop, 12.1 mi from East Side

Jordan Leigh

includes taxes & fees

10 Aug - 11 Aug

Rooftop bar, al fresco dining, open daily

The Godfrey Hotel Chicago

River North, 13.9 mi from East Side

Tanil

includes taxes & fees

9 Aug - 10 Aug

2 restaurants; breakfast, lunch and dinner served

LondonHouse Chicago, Curio Collection by Hilton

The Loop, 13.3 mi from East Side

Sophie

includes taxes & fees

9 Aug - 10 Aug

The Drake

Streeterville, 14.1 mi from East Side

Israel

includes taxes & fees

12 Aug - 13 Aug

The Buckingham Hotel

The Loop, 12.7 mi from East Side

Dominique

includes taxes & fees

19 Jul - 20 Jul

View all properties

Where to stay in East Side

Find the best East Side areas for the activities you enjoy most.

A busy city street with tall buildings, a bus, and cars.

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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A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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Top East Side Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Wonderful staff. Very helpful and courteous. Excellent location - close to theater shows, Riverwalk and shopping downtown and lake shore. Felt very safe walking at night and the security on site. The waitstaff and food were excellent - arrived one night at 9:45 pm and within five minutes had a delicious meal! Would definitely stay there again! Bed was super comfy!!!"

Warwick Allerton - Chicago

8/10 Good

"Love the location and the history of the place. The bellhops and parking valet were just wonderful. I was put off when we asked for an early check in for our niece arriving the next day and the desk clerk found a room that was already cleaned and made the arrangement. She did n ot tell me that it would be an extra $25 which I found out when we checked our niece in. Too late! The ice machine on our floor 22 was broken so we had to go to the 17th floor for ice. Not horrible but inconvenient."

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

8/10 Good

"The area around the toilet was really dirty; staff were a little rude when the elevators were out of order and it was insanely inconvenient. There are no stairs to access rooms which seems like a safety issue. Otherwise, the space of the room was a great size and location was nice for the price. Breakfast was better than most. With the exception of the toilet, I was super impressed until the last day when we felt trapped by the elevator and lack of stairs. This made us ready to leave."

Search Hotels in East Side, Chicago

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Our top choices for East Side hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Travelodge by Wyndham Downtown Chicago

Freehand Chicago

FOUND Hotels, Chicago, Series by Marriott

LIVN - West Loop Chicago

Congress Plaza Hotel

The Chicago Hotel Collection Ambassador Gold Coast

Silversmith Hotel Chicago Downtown

Palmer House a Hilton Hotel

The Chicago Hotel Collection - Magnificent Mile

The Wade

Warwick Allerton - Chicago

Best Western Grant Park Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Staypineapple, An Iconic Hotel, The Loop

Hilton Garden Inn Chicago Downtown South Loop

The Godfrey Hotel Chicago

LondonHouse Chicago, Curio Collection by Hilton

The Drake

The Buckingham Hotel

Where to stay in East Side

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top East Side Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

Frequently asked questions

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