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 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

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 21.3 km from East Side

Julie

CA $437 total

includes taxes & fees

Aug 17 - Aug 18

2. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 19.5 km from East Side

Jordan Leigh

CA $286 total

includes taxes & fees

Aug 18 - Aug 19

3. Best Western Grant Park Hotel

The Loop, 19.5 km from East Side

Tammy

CA $276 total

includes taxes & fees

Aug 16 - Aug 17

Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

4. Holiday Inn & Suites Chicago - Downtown by IHG

West Loop, 20.6 km from East Side

Terrell

CA $262 total

includes taxes & fees

Aug 9 - Aug 10

5. Travelodge by Wyndham Downtown Chicago

The Loop, 20.1 km from East Side

MARTINA

CA $248 total

includes taxes & fees

Aug 19 - Aug 20

6. Freehand Chicago

River North, 22 km from East Side

Clifton

CA $258 total

includes taxes & fees

Jul 28 - Jul 29

Suite, 1 Bedroom, Corner | Private kitchen

7. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 19.5 km from East Side

jayne

CA $309 total

includes taxes & fees

Aug 19 - Aug 20

8. Le Méridien Essex Chicago

The Loop, 19.8 km from East Side

Robert

CA $317 total

includes taxes & fees

Aug 9 - Aug 10

9. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Loop, 20.3 km from East Side

Aleace

CA $305 total

includes taxes & fees

Aug 9 - Aug 10

10. Silversmith Hotel Chicago Downtown

Theatre District, 20.9 km from East Side

Donilyn

CA $309 total

includes taxes & fees

Aug 9 - Aug 10

11. Congress Plaza Hotel

The Loop, 20.1 km from East Side

ERIC

CA $293 total

includes taxes & fees

Aug 10 - Aug 11

12. The Chicago Hotel Collection - Magnificent Mile

Streeterville, 22.2 km from East Side

Precious

CA $271 total

includes taxes & fees

Aug 9 - Aug 10

55-inch LCD TV with cable channels, TV, pay movies

13. L7 Chicago by LOTTE

Theatre District, 21.4 km from East Side

Julie Ann

CA $314 total

includes taxes & fees

Aug 17 - Aug 18

14. Hilton Chicago

The Loop, 19.9 km from East Side

Nicole M

CA $559 total

includes taxes & fees

Aug 3 - Aug 4

15. Hilton Garden Inn Chicago Central Loop

The Loop, 20.8 km from East Side

Malachi

CA $340 total

includes taxes & fees

Aug 9 - Aug 10

Presidential Suite, 1 Bedroom, Non Smoking

16. Hotel 55 Chicago Downtown

River North, 22 km from East Side

Matt

CA $302 total

includes taxes & fees

Jul 26 - Jul 27

17. Crowne Plaza Chicago West Loop by IHG

21.5 km from East Side

Bethany

CA $319 total

includes taxes & fees

Aug 20 - Aug 21

18. The Allegro Royal Sonesta Hotel Chicago Loop

Theatre District, 21.4 km from East Side

Robert

CA $355 total

includes taxes & fees

Aug 16 - Aug 17

19. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 21.1 km from East Side

Diana

CA $322 total

includes taxes & fees

Aug 9 - Aug 10

20. Club Quarters Hotel, Central Loop, Chicago

Theatre District, 20.8 km from East Side

Tamara

CA $272 total

includes taxes & fees

Aug 16 - Aug 17

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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

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

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

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

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

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Great views!"

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"The art deco design of the hotel is lovely and the location is perfect for exploring the Loop. But the staff are the reason we will come back! After we checked out we realized that we left food in the refridgerator - leftovers from a restaurant that makes the most amazing mole. I called the hotel and thankfully our room had not yet been cleaned, so the staff kindly held our food at reception until we could come back to pick it up. The also graciously did not make fun of us for being that obsessed with mole."

Eurostars Magnificent Mile

8/10 Good

"Hotel room was nice, not very big but still had everything that was needed. AC worked just fine as well. The area was great, lots of things around. The subway is about a 4 minute walk which makes using public transportation a lot easier. Most tourist areas are about a 20 minute walk from this place!"

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

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

2. Hilton Garden Inn Chicago Downtown South Loop

3. Best Western Grant Park Hotel

4. Holiday Inn & Suites Chicago - Downtown by IHG

5. Travelodge by Wyndham Downtown Chicago

6. Freehand Chicago

7. Homewood Suites by Hilton Chicago Downtown South Loop

8. Le Méridien Essex Chicago

9. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

10. Silversmith Hotel Chicago Downtown

11. Congress Plaza Hotel

12. The Chicago Hotel Collection - Magnificent Mile

13. L7 Chicago by LOTTE

14. Hilton Chicago

15. Hilton Garden Inn Chicago Central Loop

16. Hotel 55 Chicago Downtown

17. Crowne Plaza Chicago West Loop by IHG

18. The Allegro Royal Sonesta Hotel Chicago Loop

19. La Quinta Inn & Suites by Wyndham Chicago Downtown

20. Club Quarters Hotel, Central Loop, Chicago

Where to stay in East Side

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top East Side Hotel Reviews

The Royal Sonesta Chicago Downtown

Frequently asked questions

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