Hotels in Uptown

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4 Oct - 5 Oct
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10 Oct - 12 Oct
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17 Oct - 19 Oct

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Top 10 Hotels in Uptown

The Guesthouse Hotel
Rooftop terrace

The Guesthouse Hotel

4.0 star property
9.8 out of 10, Exceptional, (348)
"It’s across a cemetery which made the stay a little eerie. "
The price is S$364
includes taxes & fees
3 Nov - 4 Nov
The Guesthouse Hotel
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3904)
"Great place to stay. "
The price is S$262
includes taxes & fees
4 Nov - 5 Nov
citizenM Chicago Downtown
River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4710)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is S$331
includes taxes & fees
6 Oct - 7 Oct
River Hotel
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2166)
"Great hotel "
The price is S$327
includes taxes & fees
2 Nov - 3 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2077)
"Great hotel"
The price is S$241
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3058)
"Perfect location, walkable to many restaurants and shops"
The price is S$166
includes taxes & fees
3 Nov - 4 Nov
Eurostars Magnificent Mile
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (3018)
"Enjoyed our stay"
The price is S$219
includes taxes & fees
3 Nov - 4 Nov
Hilton Chicago/Magnificent Mile Suites
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2844)
"Had a great stay!"
The price is S$222
includes taxes & fees
2 Nov - 3 Nov
Aloft Chicago Mag Mile
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9300)
"Beautiful hotel!"
Congress Plaza Hotel
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2416)
"Great walkable location to all the sights! "
The price is S$194
includes taxes & fees
27 Oct - 28 Oct
Freehand Chicago
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2240)
"Very nice hotel "
The price is S$316
includes taxes & fees
23 Oct - 24 Oct
Hilton Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (4026)
"We definitely will stay there again place was very nice "
The price is S$271
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Chicago Downtown/Magnificent Mile
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.0 out of 10, Very good, (263)
"Loved this place if you want something affordable and nice! "
The price is S$140
includes taxes & fees
5 Nov - 6 Nov
FOUND Hotel Chicago River North
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2533)
"Location is great and the breakfast buffet is amazing"
The price is S$279
includes taxes & fees
3 Nov - 4 Nov
Hotel Riu Plaza Chicago
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2161)
"The hotel was quiet and clean and restaurant was right next door in addition to inside the hotel"
The price is S$338
includes taxes & fees
23 Oct - 24 Oct
Hyatt Centric The Loop Chicago
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1018)
"Great stay"
The price is S$192
includes taxes & fees
2 Nov - 3 Nov
Best Western River North Hotel
LondonHouse Chicago, Curio Collection by Hilton
Lobby

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
9.4 out of 10, Exceptional, (3351)
"Excellent location and views from the hotel "
The price is S$304
includes taxes & fees
30 Oct - 31 Oct
LondonHouse Chicago, Curio Collection by Hilton
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.4 out of 10, Exceptional, (3355)
"Great place to stay "
The price is S$416
includes taxes & fees
30 Oct - 31 Oct
Hyatt Regency Chicago
voco Chicago Downtown - Riverwalk by IHG
Bar (on property)

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
8.8 out of 10, Excellent, (3176)
"Great stay "
The price is S$322
includes taxes & fees
19 Oct - 20 Oct
voco Chicago Downtown - Riverwalk by IHG
Warwick Allerton - Chicago
Lobby sitting area

Warwick Allerton - Chicago

4.0 star property
8.4 out of 10, Very good, (2897)
"Great location, friendly staff."
The price is S$171
includes taxes & fees
3 Nov - 4 Nov
Warwick Allerton - 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 which includes 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 featuring a river or creek

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.

Chicago which includes a city and modern architecture

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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Good place to stay, will come back."
Tan Phuc 3-night trip
Posted 1 day ago
Hilton Chicago/Magnificent Mile Suites

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 40 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.