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
Save 100% on your flight
Price was $757, price is now $484 per person
$484
per person
Jul 10 - Jul 14
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,127, price is now $582 per person
$582
per person
Jul 10 - Jul 14
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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 $1,133, price is now $710 per person
$710
per person
Jul 10 - Jul 14
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,560, price is now $986 per person
$986
per person
Jul 10 - Jul 14
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,715, price is now $1,086 per person
$1,086
per person
Jul 10 - Jul 14
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
The Godfrey Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,159, price is now $738 per person
$738
per person
Jul 10 - Jul 14
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
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. ...
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 Sturtevant / Racine / Mount Pleasant
13340 Hospitality Ct Mount Pleasant WI
18.51 km from Uptown
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 ...
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 The People's Choice Family ...
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 ...
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 ...
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 ...
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 ...
Courtyard Chicago Waukegan Gurnee
3800 Northpoint Blvd Waukegan IL
26.16 km from Uptown
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 ...
Antioch Hotel & Suites
350 Illinois 173 Antioch IL
24.09 km from Uptown
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. ...
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 ...
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 ...
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.
Sun, May 10 - Sun, May 24
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$170 Roundtrip, found 4 days ago
$170
Roundtrip
found 4 days ago
Wed, May 6 - Tue, May 26
DEN
Denver Intl.
MKE
General Mitchell Intl.
$293 Roundtrip, found 18 hours ago
$293
Roundtrip
found 18 hours ago
Fri, May 29 - Tue, Jun 2
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Wed, May 6 - Tue, May 26
DEN
Denver Intl.
MKE
General Mitchell Intl.
$303 Roundtrip, found 18 hours ago
$303
Roundtrip
found 18 hours ago
Wed, May 6 - Tue, May 26
DEN
Denver Intl.
MKE
General Mitchell Intl.
$313 Roundtrip, found 18 hours ago
$313
Roundtrip
found 18 hours ago