A frozen river with a city skyline in the background.

Find All Inclusive Resorts and Hotels in Uptown, Chicago

  • 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 availability on Uptown All Inclusive Resorts and Hotels

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

Our top choices for Uptown all-inclusive hotels

A rooftop terrace with a brick wall, large windows, and a metal railing.

1. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is CA $106
CA $351 total
includes taxes & fees
Nov 9 - Nov 10
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A rooftop patio with outdoor seating, a pergola, and a city skyline view.

2. The Guesthouse Hotel

The Guesthouse Hotel
4.0 star property
Uptown
9.8 out of 10, Exceptional, (429 reviews)
"Well equipped kitchen, comfortable bedrooms, very friendly staff"
United States
Kathryn
The price is CA $426
CA $500 total
includes taxes & fees
Nov 29 - Nov 30
The Guesthouse Hotel
A rooftop terrace with a brick wall, large windows, and a metal railing.

3. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is CA $106
CA $351 total
includes taxes & fees
Nov 9 - Nov 10
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern kitchen with dark blue cabinets, stainless steel appliances, and a white countertop.

4. Elegant 2BR Apartment w/ In-Unit Laundry

Elegant 2BR Apartment w/ In-Unit Laundry
Uptown
The price is CA $134
CA $300 total
includes taxes & fees
Dec 7 - Dec 8
Elegant 2BR Apartment w/ In-Unit Laundry
A bathroom with a toilet, a sink, a shower curtain, and a mat.

5. Delightful 1BR Apt in Ravenswood

Delightful 1BR Apt in Ravenswood
Uptown
The price is CA $99
CA $298 total
includes taxes & fees
Nov 9 - Nov 10
Delightful 1BR Apt in Ravenswood
A bedroom with a bed, a nightstand, a desk, a chair, a ceiling fan, and a TV.

6. Sunny Studio in Heart of Ravenswood

Sunny Studio in Heart of Ravenswood
Uptown
10.0 out of 10, Exceptional, (1 review)
"."
United States
Patrick V.
The price is CA $89
CA $272 total
includes taxes & fees
Nov 9 - Nov 10
Sunny Studio in Heart of Ravenswood
A modern living room with a green sectional sofa, a patterned rug, and artwork on the walls.

7. The Velvet Manor | 2BR Boutique Stay

The Velvet Manor | 2BR Boutique Stay
Uptown
10.0 out of 10, Exceptional, (3 reviews)
"The place was amazing! Hosts were super responsive and helpful.Would stay there again."
United States
Nicole C.
The price is CA $172
CA $763 total
includes taxes & fees
Nov 17 - Nov 18
The Velvet Manor | 2BR Boutique Stay
A modern living room with a sectional sofa, a round coffee table, and a large painting on the wall.

8. Refined 3BR Andersonville manor with garage, Jacuzzi, and private outdoor space.

Refined 3BR Andersonville manor with garage, Jacuzzi, and private outdoor space.
Uptown
10.0 out of 10, Exceptional, (1 review)
"First, the place is beautiful. The location is pretty perfect too. I'm a big fan of dining out and there were some fantastic spots walkable, so that was a big plus. The host was communicative and friendly. The little welcome gifts were a nice perk too. Will definitely be back next time I'm in town."
United States
Collin M.
The price is CA $340
CA $1,039 total
includes taxes & fees
Dec 2 - Dec 3
Refined 3BR Andersonville manor with garage, Jacuzzi, and private outdoor space.
A covered porch with wicker furniture, a table, and a railing.

9. Spacious Chicago Group Home! Walk to Train & Eats

Spacious Chicago Group Home! Walk to Train & Eats
Uptown
10.0 out of 10, Exceptional, (4 reviews)
"Perfect for us to stay for the weekend of the marathon with my son and a few of his friends."
United States
Jeffrey K.
The price is CA $349
CA $1,036 total
includes taxes & fees
Nov 9 - Nov 10
Spacious Chicago Group Home! Walk to Train & Eats
A luxurious bathroom with a large oval bathtub, a chandelier, and two large mirrors with floral arrangements.

10. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 7.8 km from Uptown
8.4 out of 10, Very good, (3,970 reviews)
"The hotel was very nice and I enjoyed my brief stay."
United States
Cinde
The price is CA $114
CA $136 total
includes taxes & fees
Dec 7 - Dec 8
The Whitehall Hotel, BW Premier Collection
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

11. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 10.3 km from Uptown
9.6 out of 10, Exceptional, (1,221 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is CA $197
CA $234 total
includes taxes & fees
Dec 6 - Dec 7
Hilton Vacation Club Hotel Blake Chicago
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

12. 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, (5,061 reviews)
"Great place to stay"
United States
Melissa
The price is CA $143
CA $170 total
includes taxes & fees
Dec 7 - Dec 8
Hilton Chicago/Magnificent Mile Suites
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

13. 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, (2,582 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is CA $137
CA $163 total
includes taxes & fees
Dec 7 - Dec 8
DoubleTree by Hilton Chicago - Magnificent Mile
A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

14. 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, (2,775 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is CA $185
CA $269 total
includes taxes & fees
Nov 23 - Nov 24
Sable at Navy Pier Chicago, Curio Collection by Hilton
A rooftop terrace with lounge chairs and tables, offering a city skyline view.

15. Best Western River North Hotel

Best Western River North Hotel
2.5 star property
River North, 8.4 km from Uptown
7.8 out of 10, Good, (1,191 reviews)
"Good location, friendly staff!"
United States
Alexis
The price is CA $113
CA $134 total
includes taxes & fees
Dec 7 - Dec 8
Best Western River North Hotel
A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.

16. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 8.4 km from Uptown
9.0 out of 10, Wonderful, (1,958 reviews)
"Hotel is great for the price."
United States
alex
The price is CA $119
CA $142 total
includes taxes & fees
Dec 7 - Dec 8
ACME Hotel Chicago, Outset Collection by Hilton
A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

17. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
River North, 8.6 km from Uptown
9.2 out of 10, Wonderful, (1,593 reviews)
"Great hotel"
United States
Tracy
The price is CA $141
CA $168 total
includes taxes & fees
Dec 8 - Dec 9
Hampton Inn & Suites Chicago Downtown
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

18. Hotel 505 River North

Hotel 505 River North
4.5 star property
River North, 8.6 km from Uptown
9.2 out of 10, Wonderful, (3,010 reviews)
"Great stay!"
United States
Miya
The price is CA $177
CA $255 total
includes taxes & fees
Dec 9 - Dec 10
Hotel 505 River North
A modern interior with a dining area, sofas, and artwork on the walls.

19. Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 8.4 km from Uptown
8.6 out of 10, Excellent, (2,386 reviews)
"Great stay"
Canada
Robert
The price is CA $119
CA $144 total
includes taxes & fees
Dec 7 - Dec 8
Hotel Saint Clair- Magnificent Mile
A hotel room with a large window offering a city view, a bed, a desk, and a chair.

20. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 8.5 km from Uptown
9.0 out of 10, Wonderful, (2,086 reviews)
"Great location Staff was terrific"
United States
Richard
The price is CA $156
CA $185 total
includes taxes & fees
Dec 6 - Dec 7
Courtyard by Marriott 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.
View all properties

Choose what matters most at all-inclusive hotels in Uptown

5 stars
4 stars

Top Uptown Hotel Reviews

Frequently asked questions

Looking for Uptown all-inclusive resorts?
Uptown offers a host of things to see and do such as Lake Michigan and Aragon Ballroom. Look through our all-inclusive hotels where you can enjoy a host of amenities such as entertainment, kid's clubs, and of course food and beverages all included in your stay. Many of our all-inclusive hotels also feature activities such as golf, yoga, water sports, and more, which you can enjoy without any additional cost.
What is there to do near my all-inclusive resort in Uptown?
If you want to explore the area around your all-inclusive resort, visit Lake Michigan and Aragon Ballroom and see why travelers like Uptown! Other favorite attractions include Wrigley Field, Navy Pier, and Millennium Park.

Explore a world of travel with Expedia