Search Deals onUptown Vacation Packages
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago O'Hare - Rosemont by IHG
Save 100% on your flight
Price was $766, price is now $521 per person
$521
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and 2 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was $1,954, price is now $1,414 per person
$1,414
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Stay at this hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions American Family Field and Fiserv Forum are located nearby.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $2,168, price is now $1,224 per person
$1,224
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,466, price is now $926 per person
$926
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
L7 Chicago by LOTTE
Downtown Chicago
Save 100% on your flight
Price was $1,760, price is now $1,154 per person
$1,154
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,281, price is now $840 per person
$840
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Godfrey Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,753, price is now $1,160 per person
$1,160
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,907, price is now $1,301 per person
$1,301
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) 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.
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
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 ...
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. ...
Wingate by Wyndham Gurnee
6090 Gurnee Mills Blvd E Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Save an average of 15% on thousands of hotels when you're signed in
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Red Roof Inn Gurnee - Waukegan
3031 Belvidere Rd Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
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 ...
Hampton Inn Chicago - Gurnee
5550 Grand Ave 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 ...
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.
Thu, Sep 3 - Thu, Sep 10
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$221 Roundtrip, found 4 hours ago
$221
Roundtrip
found 4 hours ago
Tue, Oct 27 - Wed, Oct 28
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$240 Roundtrip, found 3 days ago
$240
Roundtrip
found 3 days ago
Fri, Sep 11 - Sat, Sep 12
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Wed, Nov 25 - Sun, Nov 29
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
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