Deals on vacations and trips to Uptown
Uptown flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Price was $1,159, price is now $528 per person
$528
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,111, price is now $577 per person
$577
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
The Emily Hotel
Downtown Chicago
Price was $2,059, price is now $1,075 per person
$1,075
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,109, price is now $1,146 per person
$1,146
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,586, price is now $968 per person
$968
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
Top Uptown hotels deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $210 total per night
$210 total
Sep 22 - Sep 23
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$184 nightly
The price is $216 total per night
$216 total
Sep 22 - Sep 23
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
Freehand Chicago
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $141 total per night
$141 total
Sep 22 - Sep 23
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
$182 nightly
The price is $214 total per night
$214 total
Sep 22 - Sep 23
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
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $179 total per night
$179 total
Oct 2 - Oct 3
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Express check-out, luggage storage, and concierge services are also on offer.
Pool
Pet friendly
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $189 total per night
$189 total
Sep 22 - Sep 23
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
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
