Uptown Hotels, 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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Filter by

Guest rating
Guest rating
Star rating

4758 Cheap Hotels in Uptown - Specials, Reviews, & Last Minute Deals

Rooftop terrace
The Guesthouse Hotel

The Guesthouse Hotel

4.0 star property
Uptown
9.8 out of 10, Exceptional, (359)
"Beautiful well kept rooms, accessible friendly staff, quiet, clean, comfortable."
United States
Susan F
The price is AU$321
includes taxes & fees
4 Jan - 5 Jan 2026
The Guesthouse Hotel
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 8.2 km from Uptown
9.0 out of 10, Wonderful, (3134)
"Amazing and will be staying again!"
United States
Angie
The price is AU$154
includes taxes & fees
4 Jan - 5 Jan 2026
Eurostars Magnificent Mile
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Streeterville, 8.6 km from Uptown
8.8 out of 10, Excellent, (2176)
"Great stay "
United States
Melinda
The price is AU$159
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 9 km from Uptown
8.8 out of 10, Excellent, (4842)
"Location of the Hotel is very nice and the hotel is very clean."
United States
Khaing
The price is AU$137
includes taxes & fees
5 Jan - 6 Jan 2026
River Hotel
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 7.8 km from Uptown
9.0 out of 10, Wonderful, (3432)
"Great hotel located in nice area."
United States
Robert
The price is AU$186
includes taxes & fees
14 Dec - 15 Dec
Hilton Chicago/Magnificent Mile Suites
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
Streeterville, 9.3 km from Uptown
9.4 out of 10, Exceptional, (2254)
"Perfect environment and location"
China
YIWEI
The price is AU$216
includes taxes & fees
23 Dec - 24 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 9.1 km from Uptown
9.4 out of 10, Exceptional, (4083)
"I enjoyed my stay with this hotel and would stay here again"
United States
Kim Leticia Terrelle
The price is AU$190
includes taxes & fees
14 Dec - 15 Dec
citizenM Chicago Downtown
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 8.5 km from Uptown
8.6 out of 10, Excellent, (2944)
"Great location and great staff!!"
United States
lynne
The price is AU$160
includes taxes & fees
11 Dec - 12 Dec
Aloft Chicago Mag Mile
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 10.7 km from Uptown
8.4 out of 10, Very good, (2344)
"We had a great stay and will be back again."
United States
Amber
The price is AU$247
includes taxes & fees
21 Dec - 22 Dec
Hilton Chicago
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
River North, 8.5 km from Uptown
8.4 out of 10, Very good, (4216)
"Great location. "
United States
Rodger
The price is AU$146
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
West Loop, 10.2 km from Uptown
8.4 out of 10, Very good, (1004)
"Amazing staff clean and secure hotel "
United States
Aniyah
The price is AU$187
includes taxes & fees
24 Dec - 25 Dec
Holiday Inn & Suites Chicago - Downtown by IHG
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 9.6 km from Uptown
9.2 out of 10, Wonderful, (2098)
"Would stay again. "
United States
Montroy
Silversmith Hotel Chicago Downtown
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.5 km from Uptown
9.0 out of 10, Wonderful, (1743)
"The location was great!!"
United States
Yvette
The price is AU$152
includes taxes & fees
14 Dec - 15 Dec
Crowne Plaza Chicago West Loop by IHG
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
River North, 8.3 km from Uptown
8.4 out of 10, Very good, (356)
"love this place definitely coming back !"
United States
Dayanara
The price is AU$104
includes taxes & fees
4 Jan - 5 Jan 2026
FOUND Hotel Chicago River North
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 8.4 km from Uptown
8.0 out of 10, Very good, (2620)
"Accommodation and great customer serbice!"
United States
Haidee
The price is AU$141
includes taxes & fees
5 Jan - 6 Jan 2026
Freehand Chicago
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 10.4 km from Uptown
8.0 out of 10, Very good, (9611)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is AU$193
includes taxes & fees
2 Jan - 3 Jan 2026
Congress Plaza Hotel
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 8.4 km from Uptown
9.4 out of 10, Exceptional, (2915)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is AU$212
includes taxes & fees
15 Dec - 16 Dec
Hotel Riu Plaza Chicago
Lobby
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
The Loop, 9 km from Uptown
9.4 out of 10, Exceptional, (3419)
"Great Hotel!"
United States
Siranush
The price is AU$232
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
Rooftop terrace
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4.0 star property
Theatre District, 9.7 km from Uptown
9.0 out of 10, Wonderful, (2270)
"Awesome place to stay that was located in the middle of everything! "
United States
Denny
The price is AU$198
includes taxes & fees
21 Dec - 22 Dec
Hyatt Centric The Loop Chicago
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 9.7 km from Uptown
8.4 out of 10, Very good, (2116)
"Loved and enjoyed our stay"
United States
Luis
The price is AU$220
includes taxes & fees
29 Dec - 30 Dec
Palmer House a Hilton Hotel
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.
View all properties

Our guide on where to stay in Uptown

Find the best Uptown areas for the activities you enjoy most.
Downtown Chicago featuring a city

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 - River North

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

The Loop - Downtown which includes a river or creek

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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.

Chicago showing rides

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 Uptown Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"nice room, great bfast at the bar"
Jon Scott 2-night trip
Posted 20 hours ago
The Royal Sonesta Chicago Downtown

Frequently asked questions

What's it like in Uptown?
Uptown is a neighbourhood that travellers like for its theatres, live music and lake views. Looking for sights you might find in a travel guide about Uptown? Consider a visit to Lake Michigan while you're in the neighbourhood.
Where is the best place to stay in Uptown?
Based on Expedia customer reviews, The Guesthouse Hotel is the highest ranked property in Uptown. This hotel offers private balconies and a fitness centre.
How many hotels will I be able to find in the Uptown area?
If you're searching for places to stay in Chicago, Expedia has something to meet your needs with 41 Uptown hotels and other accommodation options to choose from.
If I need to cancel my hotel reservation in Uptown, will I receive a refund?
Yes! Most hotel bookings are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and be given a refund within 24 hours of booking. Add dates, click "Search", then you can use the "fully refundable" filter to get the top deals on offer in Uptown.
What are the top things to see and do in Uptown?
Spend some time exploring the great outdoors at Lake Michigan, Lincoln Park and Challenger Park. Aragon Ballroom and Riviera Theatre are some other stops worth a visit in the neighbourhood. Wrigley Field, Pegasus Players and Aragon Entertainment Center are just a few of the places to visit in and around Uptown. While you're out sightseeing in Chicago, make sure that you visit other sights such as About Face Theater or Hutchinson Street Historic District.
How can I get around Uptown and the greater Chicago area?
If you want to see more of the city, Wilson Station is the closest metro stop. Others nearby include Lawrence Station and Argyle Station. If you want to head out of town, you can hop aboard a train at Chicago Ravenswood Station.

Explore a world of travel with Expedia