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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,129, price is now $664 per person
$664
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,693, price is now $957 per person
$957
per person
Jul 14 - Jul 19
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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,557, price is now $926 per person
$926
per person
Jul 14 - Jul 19
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 parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,302, price is now $829 per person
$829
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,231, price is now $828 per person
$828
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,202, price is now $810 per person
$810
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
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. ...
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 ...
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 ...
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 ...
Red Roof Inn Gurnee - Waukegan
3031 Belvidere Rd Waukegan IL
25.73 km from Uptown
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 ...
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 ...
The Stella Hotel & Ballroom
5706 8th Ave Kenosha WI
1.65 km from Uptown
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 ...
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 ...
Wyndham Garden Kenosha Harborside
5125 6th Ave Kenosha WI
2.15 km from Uptown
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
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 ...
Holiday Inn Express & Suites Zion by IHG
1100 33rd St Zion IL
15.83 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 in our reviews. Popular ...
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 ...
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 ...
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 13 - Tue, Aug 18
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$202 Roundtrip, found 8 hours ago
$202
Roundtrip
found 8 hours ago
Thu, Aug 13 - Tue, Aug 18
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$214 Roundtrip, found 8 hours ago
$214
Roundtrip
found 8 hours ago
Thu, Aug 13 - Tue, Aug 18
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$287 Roundtrip, found 8 hours ago
$287
Roundtrip
found 8 hours ago
Tue, Aug 18 - Tue, Aug 25
DAL
Love Field
MKE
General Mitchell Intl.
$287 Roundtrip, found 14 hours ago
$287
Roundtrip
found 14 hours ago
Tue, Aug 18 - Tue, Aug 25
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$297 Roundtrip, found 14 hours ago
$297
Roundtrip
found 14 hours ago