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

Gina

includes taxes & fees

14 Jun - 15 Jun

Congress Plaza Hotel

The Loop, 12.5 mi from East Side

Jennifer

includes taxes & fees

2 Jun - 3 Jun

The Chicago Hotel Collection - Magnificent Mile

Streeterville, 13.8 mi from East Side

Ontario

includes taxes & fees

23 Jun - 24 Jun

Freehand Chicago

River North, 13.7 mi from East Side

Michael

includes taxes & fees

3 Jun - 4 Jun

Travelodge by Wyndham Downtown Chicago

The Loop, 12.5 mi from East Side

Amber

includes taxes & fees

3 Jun - 4 Jun

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 14.6 mi from East Side

Robin

includes taxes & fees

22 Jun - 23 Jun

Club Quarters Hotel, Central Loop, Chicago

Theatre District, 12.9 mi from East Side

Mary

includes taxes & fees

14 Jun - 15 Jun

Silversmith Hotel Chicago Downtown

Theatre District, 13 mi from East Side

Brittany

includes taxes & fees

21 Jun - 22 Jun

Eurostars Magnificent Mile

River North, 13.8 mi from East Side

Belinda

includes taxes & fees

11 Jun - 12 Jun

The Wade

Streeterville, 13.6 mi from East Side

Molly

includes taxes & fees

2 Jun - 3 Jun

Best Western Grant Park Hotel

The Loop, 12.1 mi from East Side

cheri

includes taxes & fees

16 Jun - 17 Jun

Hotel Riu Plaza Chicago

Streeterville, 13.7 mi from East Side

sierra

includes taxes & fees

21 Jun - 22 Jun

Hilton Chicago

The Loop, 12.3 mi from East Side

Robert

includes taxes & fees

8 Jun - 9 Jun

Staypineapple, An Iconic Hotel, The Loop

Theatre District, 13.1 mi from East Side

Brenda

includes taxes & fees

14 Jun - 15 Jun

River Hotel

The Loop, 13.3 mi from East Side

Jaden

includes taxes & fees

14 Jun - 15 Jun

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Streeterville, 13.6 mi from East Side

Nicholas

includes taxes & fees

18 Jun - 19 Jun

Central Loop Hotel

Theatre District, 12.9 mi from East Side

Tasha

includes taxes & fees

14 Jun - 15 Jun

Warwick Allerton - Chicago

Streeterville, 13.8 mi from East Side

Natalia

includes taxes & fees

16 Jun - 17 Jun

Hotel Felix River North/Magnificent Mile

River North, 13.9 mi from East Side

Rodolfo

includes taxes & fees

2 Jun - 3 Jun

Millennium Hotel Knickerbocker Chicago

Streeterville, 14.1 mi from East Side

Eileen

includes taxes & fees

14 Jun - 15 Jun

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Where to stay in East Side

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

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

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

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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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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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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

Hyatt Regency McCormick Place Chicago

10/10 Excellent

"Staff was nice and helpful"

Freehand Chicago

4/10 Poor

"The Hotel is in bad need of a update & remodel. Rooms are very small and dark and Dingy. carpet is very warn. We went to the room we were given an there was some kind of very loud running contently outside the window had to go to the front desk and ask for a new room. The next room was on the same side of the building but higher up still noisy but not as bad. There are plenty of other options in the area of town would suggest checking them out."

Eurostars Magnificent Mile

6/10 Okay

"It’s clean and a nice place but further than it claims from many things- also staff wasn’t helpful and parking was set up so you basically are forced into doing the most expensive route since they would not explain where you could self park! They literally said two blocks away and no direction were given even when asked."

Hotel Riu Plaza Chicago

10/10 Excellent

"The staff is very helpful, always ready to answer any question about the hotel or about the city of Chicago. The hotel is very clean , the breakfast is very good with many choices and the staff in the restaurant is excellent. My wife and I stayed in that place for eight days and seven nights and we are very happy to be there. Also the hotel is in a very good location very close to some of the most important places of Chicago. If you want to visit the beautiful city of Chicago do not miss the opportunity to know this hotel."

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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

Hyatt Regency McCormick Place Chicago

Frequently asked questions

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