Deals on vacations and trips to Uptown
Uptown flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $747, price is now $442 per person
$442
per person
Nov 13 - Nov 16
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 Westin Michigan Avenue Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,344, price is now $608 per person
$608
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 gym, bar/lounge, and coffee shop.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $956, price is now $461 per person
$461
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,078, price is now $621 per person
$621
per person
Dec 11 - Dec 14
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.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,368, price is now $1,418 per person
$1,418
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
$145 nightly
The price is $170 total per night
$170 total
Nov 2 - Nov 3
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
Freehand Chicago
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $163 total per night
$163 total
Oct 27 - Oct 28
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$192 nightly
The price is $226 total per night
$226 total
Nov 2 - Nov 3
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $175 total per night
$175 total
Nov 2 - Nov 3
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
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $210 total per night
$210 total
Oct 19 - Oct 20
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
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Free Cancellation
$301 nightly
The price is $348 total per night
$348 total
Oct 30 - Oct 31
Total with taxes and fees
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Pool
Spa
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
