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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for East Side hotels

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

1. Congress Plaza Hotel

The Loop, 20.1 km from East Side

Manuel

CA $266 total

includes taxes & fees

Sep 27 - Sep 28

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

2. Hotel Riu Plaza Chicago

Streeterville, 22 km from East Side

Jarred

CA $458 total

includes taxes & fees

Sep 20 - Sep 21

A spacious lobby with a central coffee table, sofas, and a large mirror.

3. The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 23.4 km from East Side

Laura

CA $294 total

includes taxes & fees

Sep 21 - Sep 22

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

4. Hilton Chicago/Magnificent Mile Suites

Streeterville, 22.6 km from East Side

moussa

CA $329 total

includes taxes & fees

Oct 1 - Oct 2

A dining area with tables set for four, large windows with a view of city buildings, and a curved ceiling structure.

5. Omni Chicago Hotel

Streeterville, 22.2 km from East Side

Linda

CA $445 total

includes taxes & fees

Sep 27 - Sep 28

An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.

6. The Chicago Hotel Collection - Magnificent Mile

Streeterville, 22.2 km from East Side

Patricia

CA $209 total

includes taxes & fees

Sep 29 - Sep 30

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

7. River Hotel

The Loop, 21.5 km from East Side

steve

CA $292 total

includes taxes & fees

Sep 27 - Sep 28

A modern building with a glass facade and a curved structure.

8. Hyatt Regency O'Hare Chicago

40.7 km from East Side

Joanne

CA $280 total

includes taxes & fees

Oct 11 - Oct 12

9. The Allegro Royal Sonesta Hotel Chicago Loop

Theatre District, 21.4 km from East Side

Michaela

CA $369 total

includes taxes & fees

Sep 27 - Sep 28

A room with two chairs and a small table, a large window with a city view at night.

10. Eurostars Magnificent Mile

River North, 22.2 km from East Side

Brennique

CA $328 total

includes taxes & fees

Sep 27 - Sep 28

A luxurious hotel lobby with a plush sofa set, a large wooden bookshelf, and a central decorative pillar.

11. Freehand Chicago

River North, 22 km from East Side

Jared

CA $325 total

includes taxes & fees

Sep 23 - Sep 24

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

12. L7 Chicago by LOTTE

Theatre District, 21.4 km from East Side

christina

CA $423 total

includes taxes & fees

Oct 1 - Oct 2

A modern building with a colorful facade and a red circular seating area.

13. citizenM Chicago Downtown

Theatre District, 21.4 km from East Side

Germaine

CA $323 total

includes taxes & fees

Sep 20 - Sep 21

A dining area with a table set for four, large windows offering a cityscape view at dusk.

14. The Royal Sonesta Chicago Downtown

The Loop, 21.5 km from East Side

ShaRona

CA $441 total

includes taxes & fees

Sep 20 - Sep 21

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

15. Club Quarters Hotel, Central Loop, Chicago

Theatre District, 20.8 km from East Side

Jacqueline

CA $320 total

includes taxes & fees

Sep 27 - Sep 28

The Intercontinental hotel facade with a large American flag and a floral display.

16. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 21.8 km from East Side

Anfal

CA $549 total

includes taxes & fees

Sep 20 - Sep 21

A multi-story hotel with a prominent sign reading "Crowne Plaza."

17. Crowne Plaza Chicago West Loop by IHG

21.5 km from East Side

Phillip

CA $324 total

includes taxes & fees

Sep 20 - Sep 21

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

18. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 21.5 km from East Side

Kamal

CA $488 total

includes taxes & fees

Sep 20 - Sep 21

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

19. Embassy Suites by Hilton Chicago Downtown River North

River North, 22.1 km from East Side

Kristeen

CA $330 total

includes taxes & fees

Sep 27 - Sep 28

A large, historic building with a central courtyard surrounded by trees.

20. Hilton Chicago

The Loop, 19.9 km from East Side

Lori

CA $449 total

includes taxes & fees

Sep 11 - Sep 12

View all properties

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.

See properties

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

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.

See properties

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.

See properties

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.

See properties

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.

See properties

Top East Side Hotel Reviews

The Wade

10/10 Excellent

"My room was so clean, staff was friendly, and the hotel was in such a perfect spot for the lake, shopping, and Navy Pier. I truly can’t wait to go back! Will say parking looked pricey, but the area is very walkable and I felt very safe being out so late and walking from Soldier Stadium to The Wade, from the Riverwalk to The Wade, Navy Pier to The Wade."