Uptown

Chicago

Beautiful Chicago skyline aerial drone view from above the frozen ice and snow covering Lake Michigan with a curved hooked pier near Montrose beach with colorful orange and pink sunset clouds above.
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Stay near popular Uptown attractions

Chicago_AragonBallroom_553248621563220754

Aragon Ballroom

4.6/5 (10 reviews)
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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Uptown Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is CA $190 per night from Jun 29 to Jun 30
CA $190
CA $225 total
Jun 29 - Jun 30
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,251 reviews)
"The only negative I had with the hotel was that their food choices were limited, and there were not a lot of healthy options. I would have really appreciated more veg choices with the meals, and more salad options."

Reviewed on Jun 12, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is CA $201 per night from Jun 14 to Jun 15
CA $201
CA $239 total
Jun 14 - Jun 15
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,568 reviews)
"I"

Reviewed on Jun 12, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Jun 28 to Jun 29
CA $222
CA $253 total
Jun 28 - Jun 29
includes taxes & fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,656 reviews)
"I really liked it and recommend it."

Reviewed on Jun 12, 2026

Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is CA $355 per night from Jul 3 to Jul 4
CA $355
CA $416 total
Jul 3 - Jul 4
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,337 reviews)
"Todo estuvo muy bueno"

Reviewed on Jun 11, 2026

Hilton Chicago O'Hare Airport
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
The price is CA $218 per night from Jul 1 to Jul 2
CA $218
CA $259 total
Jul 1 - Jul 2
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,592 reviews)
"Was okay, small room with a poor view, didn’t have the rollaway bed ready had to be requested separately. Overall wasn’t terribly impressed it was an overpriced Travelodge"

Reviewed on Jun 12, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
The price is CA $155 per night from Jul 5 to Jul 6
CA $155
CA $251 total
Jul 5 - Jul 6
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (3,097 reviews)
"Room was clean, staff friendly"

Reviewed on Jun 12, 2026

Freehand Chicago
See all 4,605 properties in Uptown
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 Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
Learn more about Uptown

Downtown Chicago

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile

Michigan Avenue and Chicago Water Tower are just a few worthwhile attractions to visit in Magnificent Mile. Travelers also love the fascinating museums, panoramic lake views, and popular shops.

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops, and acclaimed art galleries.

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

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Uptown

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