Hotels in Uptown

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Check prices for these dates

This weekend
22 May - 24 May
Next weekend
29 May - 31 May

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Our top choices for Uptown hotels

Rooftop terrace

The Guesthouse Hotel

The Guesthouse Hotel
4.0 star property
Uptown
9.8 out of 10, Exceptional, (398 reviews)
"Great property with clean, modern and spacious rooms and friendly and attentive staff. "
United States
Regina Therese
The price is S$392
includes taxes & fees
27 May - 28 May
The Guesthouse Hotel
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, (2,508 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is S$338
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 8.5 km from Uptown
8.0 out of 10, Very good, (3,025 reviews)
"Great central location, lots to do nearby."
United States
Michael
The price is S$158
includes taxes & fees
25 May - 26 May
Freehand Chicago
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 10.4 km from Uptown
8.0 out of 10, Very good, (10,171 reviews)
"The bar was very welcoming and the historic ambience and location was exceptional"
United States
Patricia
The price is S$203
includes taxes & fees
26 May - 27 May
Congress Plaza Hotel
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Uptown
8.6 out of 10, Excellent, (2,802 reviews)
"Great staff and location. "
United States
Robert
The price is S$340
includes taxes & fees
25 May - 26 May
Hilton Chicago
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 7 km from Uptown
8.2 out of 10, Very good, (1,478 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is S$264
includes taxes & fees
2 Jun - 3 Jun
The Chicago Hotel Collection Ambassador Gold Coast
Room service – dining

The Wade

The Wade
4.5 star property
Streeterville, 8.6 km from Uptown
8.4 out of 10, Very good, (1,835 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is S$231
includes taxes & fees
25 May - 26 May
The Wade
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 9 km from Uptown
8.8 out of 10, Excellent, (5,186 reviews)
"excellent stay"
United States
Jaeyoung
The price is S$192
includes taxes & fees
25 May - 26 May
River Hotel
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, (2,241 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is S$220
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.2 km from Uptown
7.8 out of 10, Good, (1,447 reviews)
"Great stay"
United States
Christa
The price is S$184
includes taxes & fees
25 May - 26 May
The Chicago Hotel Collection - Magnificent Mile
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, (4,201 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is S$263
includes taxes & fees
25 May - 26 May
Hotel Riu Plaza Chicago
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 11 km from Uptown
8.8 out of 10, Excellent, (1,998 reviews)
"Great location and clean room"
United States
Hyacinthe
The price is S$241
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Chicago Downtown South Loop
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 10.4 km from Uptown
7.4 out of 10, Good, (2,602 reviews)
"Staff was friendly and helpful.. location was great"
United States
Amber
The price is S$172
includes taxes & fees
25 May - 26 May
Travelodge by Wyndham Downtown Chicago
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
9.2 km from Uptown
9.0 out of 10, Wonderful, (3,334 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
United States
Saleem
The price is S$299
includes taxes & fees
25 May - 26 May
Swissotel - Chicago
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 9.7 km from Uptown
8.6 out of 10, Excellent, (2,459 reviews)
"My favorite place to stay!"
United States
Teresa
The price is S$318
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.2 km from Uptown
9.0 out of 10, Wonderful, (3,557 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Australia
Belinda
The price is S$243
includes taxes & fees
25 May - 26 May
Eurostars Magnificent Mile
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 9.3 km from Uptown
8.8 out of 10, Excellent, (2,163 reviews)
"Great place"
United States
JOSE
The price is S$371
includes taxes & fees
26 May - 27 May
Fairmont Chicago at Millennium Park
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 9.4 km from Uptown
9.4 out of 10, Exceptional, (1,068 reviews)
"Clean rooms, comfy bed."
United States
Brenda
The price is S$295
includes taxes & fees
25 May - 26 May
Staypineapple, An Iconic Hotel, The Loop
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 8.5 km from Uptown
8.6 out of 10, Excellent, (3,237 reviews)
"Nice place to stay"
United States
Jimmie
The price is S$242
includes taxes & fees
25 May - 26 May
Aloft by Marriott Chicago Mag Mile
Bathroom

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 9.2 km from Uptown
9.2 out of 10, Wonderful, (1,405 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
United States
Erik
The price is S$314
includes taxes & fees
26 May - 27 May
Sports Illustrated Resorts Chicago
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.
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Where to stay in Uptown

Find the best Uptown 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.

Magnificent Mile

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

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.

Panoramic view of Lincoln Park and the Chicago skyline.

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.

Top Uptown Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Breakfast bar was very good just need 0to go cups for coffee.I'm "
Allison 4-night trip
Posted 5 hours ago
Hotel Riu Plaza Chicago

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 44 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.

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