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.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $1,147, price is now $861 per person
$861
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff 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 $1,936, price is now $1,103 per person
$1,103
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Columbia (CAE) 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,427, price is now $893 per person
$893
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Columbia (CAE) 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.
There wasn't any coffee machine, or refrigerator or even cups in the room. However, they did have water bottles for $8 each.
The fitness center was great! The staff was great! Maybe that was why I was surprised at the lack of convenience items - though I don't know that I've ever been in a room without one.
Reviewed on Jul 24, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,481, price is now $1,045 per person
$1,045
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Columbia (CAE) 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.
Excellent location. My grandson (3.5 yeas old) and I thoroughly enjoy our daily routine of strolling along the lakeside, having meals, playing games, watching the fireworks and taking in the scenery. The room is clean and the staffs are nice. We spent a wonderful six-day vacation.
Reviewed on Jul 24, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,554, price is now $1,115 per person
$1,115
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Columbia (CAE) 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.
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,333, price is now $985 per person
$985
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Columbia (CAE) 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.
Top Hotel Deals
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
23.24 km from Uptown
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. ...
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
23.81 km from Uptown
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 ...
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
9.48 km from Uptown
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 Pleasant Prairie Kenosha
7540 118th Ave Pleasant Prairie WI
9.1 km from Uptown
Book a stay at this family-friendly hotel in Pleasant Prairie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr Waukegan IL
27.43 km from Uptown
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 ...
The Inn on Sheridan
2723 Sheridan Rd Zion IL
14.86 km from Uptown
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 ...
Days Inn by Wyndham Waukegan
630 N Green Bay Road Waukegan IL
23.4 km from Uptown
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 ...
Americas Best Value Inn & Suites Racine
5419 Durand Ave Mount Pleasant WI
13.24 km from Uptown
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 ...
Hampton Inn Chicago - Gurnee
5550 Grand Ave Gurnee IL
23.49 km from Uptown
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 ...
Country Inn & Suites by Radisson Kenosha - Pleasant Prairie
7011 122nd Ave Kenosha WI
9.42 km from Uptown
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 ...
Illinois Beach Hotel
100 Lake Front Dr Zion IL
17.34 km from Uptown
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Illinois ...
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road Grayslake IL
29.96 km from Uptown
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 ...
Wingate by Wyndham Gurnee
6090 Gurnee Mills Blvd E Gurnee IL
23.25 km from Uptown
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
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.
Thu, Aug 20 - Tue, Aug 25
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Thu, Aug 20 - Tue, Aug 25
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Thu, Aug 20 - Tue, Aug 25
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Thu, Aug 20 - Tue, Aug 25
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Thu, Aug 20 - Tue, Aug 25
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago