Search Deals onUptown Vacation Packages
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Comfort Inn
Save 100% on your flight
Price was $410, price is now $292 per person
$292
per person
May 28 - Jun 1
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Princeton. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bureau County Fairgrounds and Soldiers and Sailors Memorial are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $861, price is now $523 per person
$523
per person
May 9 - May 13
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,147, price is now $712 per person
$712
per person
May 12 - May 16
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $935, price is now $593 per person
$593
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
Price was $836, price is now $537 per person
$537
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
Holiday Inn Express & Suites Prospect Heights by IHG
Save 100% on your flight
Price was $551, price is now $354 per person
$354
per person
May 17 - May 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Prospect Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions River Trail Nature Center and Northbrook Sports Complex are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,642, price is now $1,075 per person
$1,075
per person
May 22 - May 26
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $939, price is now $636 per person
$636
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
3-4 Night Vacations in Uptown
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Uptown
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Uptown
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
Book a stay at this family-friendly resort in Gurnee. Enjoy 6 indoor pools, 5 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. ...
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant
13340 Hospitality Ct Mount Pleasant WI
Book a stay at this business-friendly hotel in Mount Pleasant. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Save an average of 15% on thousands of hotels when you're signed in
Days Inn by Wyndham Waukegan
630 N Green Bay Road Waukegan IL
Stay at this motel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Six Flags Great America and The People's Choice Family ...
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road Grayslake IL
Book a stay at this business-friendly hotel in Grayslake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Country Inn & Suites by Radisson Kenosha - Pleasant Prairie
7011 122nd Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Stella Hotel & Ballroom
5706 8th Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, May 5 - Fri, May 8
DEN
Denver Intl.
MKE
General Mitchell Intl.
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Thu, May 7 - Sun, May 17
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$144 Roundtrip, found 16 hours ago
$144
Roundtrip
found 16 hours ago
Thu, Apr 23 - Wed, May 6
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$180 Roundtrip, found 12 hours ago
$180
Roundtrip
found 12 hours ago
Sat, Apr 18 - Mon, Apr 27
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$194 Roundtrip, found 5 days ago
$194
Roundtrip
found 5 days ago
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