Deals on vacations and trips to Uptown
Uptown flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $284 per person
$284
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
Art Villa
West Town
Save 100% on your flight
Price was $999, price is now $514 per person
$514
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,779, price is now $1,084 per person
$1,084
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the indoor pool and perks like a free area shuttle.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $640, price is now $398 per person
$398
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $517 per person
$517
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Top Uptown hotels deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
$143 nightly
The price is $168 total per night
$168 total
Nov 9 - Nov 10
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $137 total per night
$137 total
Nov 16 - Nov 17
Total with taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
Freehand Chicago
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $100 total per night
$100 total
Nov 10 - Nov 11
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $154 total per night
$154 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
$128 nightly
The price is $151 total per night
$151 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$176 nightly
The price is $207 total per night
$207 total
Nov 20 - Nov 21
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.
Pet friendly
Air conditioning
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.
Popular places to visit
Montrose Beach
If a restful vacation is part of your travel plans, Montrose Beach might be the perfect place to seek out during your trip to Chicago. Stroll along the lakeside or discover the area's sunrises.
Lincoln Park
This expansive public park along Lake Michigan offers museums, beaches, nature reserves and sporting facilities.
Montrose Harbor
Explore the waterfront in Chicago with a trip to Montrose Harbor. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
Frequently asked questions
Photos of local treasures
Browse Uptown vacation photos for more inspiration
