East Side hotels in Chicago

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for East Side hotels

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 22 km from East Side
8.0 out of 10, Very good, (2670)
"It's an excellent place."
United States
Jose
The price is HK$377
HK$580 total
includes taxes & fees
5 Jan - 6 Jan 2026
Freehand Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 21.5 km from East Side
8.8 out of 10, Excellent, (4878)
"Clean friendly hotel "
United States
maria
The price is HK$634
HK$745 total
includes taxes & fees
12 Jan - 13 Jan 2026
River Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 20.1 km from East Side
8.0 out of 10, Very good, (9723)
"Wonderful stay!"
United States
Zach
The price is HK$1,952
HK$2,292 total
includes taxes & fees
31 Dec - 1 Jan 2026
Congress Plaza Hotel

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 21.9 km from East Side
8.6 out of 10, Excellent, (3001)
"Great place to stay"
United States
Elisha
The price is HK$637
HK$748 total
includes taxes & fees
22 Jan - 23 Jan 2026
Aloft Chicago Mag Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 21.8 km from East Side
8.8 out of 10, Excellent, (2215)
"It was a beautiful stay "
United States
Donald
The price is HK$663
HK$778 total
includes taxes & fees
6 Jan - 7 Jan 2026
DoubleTree by Hilton Chicago - Magnificent Mile

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 21.3 km from East Side
9.4 out of 10, Exceptional, (2294)
"Great stay!"
United States
Angela
The price is HK$665
HK$1,045 total
includes taxes & fees
20 Jan - 21 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 21.4 km from East Side
9.4 out of 10, Exceptional, (3409)
"The Hotel was amazing great location "
United States
Donnisha
The price is HK$1,119
HK$1,542 total
includes taxes & fees
20 Jan - 21 Jan 2026
Hyatt Regency Chicago

The Wade

The Wade
4.5 star property
Streeterville, 21.8 km from East Side
8.4 out of 10, Very good, (1551)
"All was great room view and staff "
United States
STANLEY
The price is HK$723
HK$848 total
includes taxes & fees
19 Jan - 20 Jan 2026
The Wade

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 20.8 km from East Side
8.8 out of 10, Excellent, (3338)
"Great hotel "
United States
Anthony
The price is HK$634
HK$744 total
includes taxes & fees
12 Jan - 13 Jan 2026
Club Quarters Hotel, Central Loop, Chicago

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
River North, 21.9 km from East Side
8.6 out of 10, Excellent, (4295)
"Amazing staff and perfect location "
United States
Brandi
The price is HK$586
HK$688 total
includes taxes & fees
26 Jan - 27 Jan 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 21.7 km from East Side
8.2 out of 10, Very good, (2778)
"Excellent place to stay "
United States
Teniesha
The price is HK$643
HK$983 total
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 21.5 km from East Side
8.8 out of 10, Excellent, (2022)
"Great stay"
United States
Kramer
The price is HK$634
HK$745 total
includes taxes & fees
12 Jan - 13 Jan 2026
Club Quarters Hotel Wacker at Michigan, Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 19.9 km from East Side
8.4 out of 10, Very good, (2444)
"What a great stay!!"
United States
Alejandra
The price is HK$950
HK$1,343 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hilton Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Magnificent Mile, 22.2 km from East Side
8.4 out of 10, Very good, (3019)
"Every thing is perfect, the location, safe for solo travel. "
United States
Ken
The price is HK$484
HK$797 total
includes taxes & fees
12 Jan - 13 Jan 2026
Warwick Allerton - Chicago

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 22.6 km from East Side
8.2 out of 10, Very good, (3819)
" Breakfast is good, location is excellent, service staff is courteous."
United States
Luis
The price is HK$595
HK$698 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Whitehall Hotel, BW Premier Collection

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 22 km from East Side
9.4 out of 10, Exceptional, (3080)
"Excellent stay great location and great rooms"
United States
Joseph
The price is HK$775
HK$1,128 total
includes taxes & fees
26 Jan - 27 Jan 2026
Hotel Riu Plaza Chicago

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 21.5 km from East Side
9.4 out of 10, Exceptional, (3470)
"Great hotel! "
United States
Kianna
The price is HK$1,077
HK$1,264 total
includes taxes & fees
6 Jan - 7 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 21.2 km from East Side
9.2 out of 10, Wonderful, (1917)
"Great location, friendly staff rooms were great and clean."
United States
Derrick
The price is HK$637
HK$979 total
includes taxes & fees
15 Jan - 16 Jan 2026
Arlo Chicago

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
River North, 21.9 km from East Side
8.8 out of 10, Excellent, (3539)
"Great location and breakfast.. can be a bit pricey but worth it. "
Canada
Shaurya
The price is HK$894
HK$1,049 total
includes taxes & fees
15 Jan - 16 Jan 2026
voco Chicago Downtown - Riverwalk by IHG

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 22 km from East Side
9.0 out of 10, Wonderful, (1052)
"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "
United States
Rebecca
The price is HK$762
HK$1,122 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Where to stay in East Side

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

Magnificent Mile

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

The Loop

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

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.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top East Side Hotel Reviews

Frequently asked questions

What's it like in East Side?
East Side is a neighbourhood that travellers like for its restaurants and parks. Looking for sights you might find in a travel guide about East Side? Consider a visit to Lake Michigan while you're in the neighbourhood.
If I need to cancel my hotel reservation in East Side, will I receive a refund?
Yes! You'll find that most room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to cancel it and get a refund within a 24-hour period of booking. Enter your dates, click on "Search", then you can use the "fully refundable" filter to get top deals in East Side.
What are the top things to see and do in East Side?
Spend some time exploring the natural setting of East Side with a visit to Lake Michigan and Calumet Park. Munson Beach and Calumet Beach are also a couple of places to visit in the neighbourhood. Hammond Marina Beach, Whihala Beach and Horseshoe Hammond Casino are just a few of the places to visit in and around East Side. While you're out sightseeing, The Venue at Horseshoe Hammond and Mahalia Jackson Residence are a couple of additional sights to visit in Chicago.

Explore a world of travel with Expedia