Uptown Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Uptown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$486
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Tulsa (TUL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
This hotel isn't worthy of 4 stars, room is basic, shower tray drips, it's not a luxury hotel and 4* is an exaggeration/ generous compared to the price point of the room.
Staff at front desk were reactive rather than pro-active, the would watch you go to the bar but remain at their seats at the front desk knowing the bar was unmanned and you would have to go and prompt them. Breakfast was poor.
Reviewed on Oct 23, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$592
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Tulsa (TUL) 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.
The Talbott, Autograph Collection
Downtown Chicago
$630
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Tulsa (TUL) 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Nice property overall
Room was very nice
Location excellent
Reviewed on Oct 19, 2026
Swissotel - Chicago
Downtown Chicago
$603
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Tulsa (TUL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
$639
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Tulsa (TUL) 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.
Arlo Chicago
Downtown Chicago
$551
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Tulsa (TUL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Very nice hotel.
Reviewed on Oct 22, 2026
Top Hotel Deals
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 ...
The Inn on Sheridan
2723 Sheridan Rd Zion IL
Book a stay at this business-friendly hotel in Zion. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
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 ...
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. ...
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 ...
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 ...
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 ...
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 ...
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 ...
Antioch Hotel & Suites
350 Illinois 173 Antioch IL
Book a stay at this business-friendly hotel in Antioch. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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 Gurnee Mills are located ...
Courtyard Chicago Waukegan Gurnee
3800 Northpoint Blvd Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Super 8 by Wyndham Sturtevant/Racine
910 S Sylvania Ave Sturtevant WI
Book a stay at this business-friendly hotel in Sturtevant. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise 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 ...
Americas Best Value Inn & Suites Racine
5419 Durand Ave Mount Pleasant WI
Book a stay at this business-friendly hotel in Mount Pleasant. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Nov 27 - Tue, Dec 1
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$211
Roundtrip
found 17 hours ago
Thu, Nov 26 - Wed, Dec 2
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$265
Roundtrip
found 17 hours ago
Fri, Nov 27 - Tue, Dec 1
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$268
Roundtrip
found 17 hours ago
Fri, Nov 27 - Tue, Dec 1
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$279
Roundtrip
found 17 hours ago
Sat, Nov 21 - Wed, Nov 25
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$285
Roundtrip
found 4 days ago
Best points of interest in Kenosha
- Naval Base Great Lakes Vacations
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- Genesee Theater Vacations
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