Trevor Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Trevor Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,241, price is now $759 per person
$759
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip 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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,841, price is now $1,016 per person
$1,016
per person
Jun 3 - Jun 7
found 9 hours ago
Roundtrip flight included
Boston (BOS) 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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,942, price is now $1,108 per person
$1,108
per person
Jun 3 - Jun 7
found 9 hours ago
Roundtrip flight included
Boston (BOS) 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 $1,344, price is now $775 per person
$775
per person
Jul 4 - Jul 11
found 20 hours ago
Roundtrip flight included
Boston (BOS) 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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,401, price is now $862 per person
$862
per person
Jun 3 - Jun 7
found 9 hours ago
Roundtrip flight included
Boston (BOS) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,739, price is now $1,107 per person
$1,107
per person
Jun 3 - Jun 7
found 9 hours ago
Roundtrip flight included
Boston (BOS) 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.
Top Hotel Deals
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
20.36 km from city center
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. ...
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
26.99 km from city center
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the helpful staff in ...
The Cove Of Lake Geneva
111 Center St Lake Geneva WI
26.98 km from city center
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy an outdoor pool, 2 hot tubs, and room service. Our guests praise the pool and the helpful staff ...
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
25.16 km from city center
Book a stay at this spa aparthotel in Lake Geneva. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
20.85 km from city center
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 Waukegan
630 N Green Bay Road Waukegan IL
25.25 km from city center
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 ...
Holiday Inn Club Vacations at Lake Geneva Resort by IHG
7036 Grand Geneva Way Lake Geneva WI
25.7 km from city center
Book a stay at this spa resort in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
Motel 6 Libertyville, IL
1809 N Milwaukee Ave Libertyville IL
26.38 km from city center
Book a stay at this business-friendly motel in Libertyville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in ...
Days Inn by Wyndham Pleasant Prairie Kenosha
7540 118th Ave Pleasant Prairie WI
15.25 km from city center
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 ...
Lodge Geneva National
W4240 WI-50 Lake Geneva WI
32.74 km from city center
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant ...
Sonesta Simply Suites Chicago Libertyville
1100 N Us Route 45 Libertyville IL
25.94 km from city center
Book a stay at this business-friendly hotel in Libertyville. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff ...
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road Grayslake IL
21.64 km from city center
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 ...
Sonesta Simply Suites Chicago Waukegan
1151 S Waukegan Rd Waukegan IL
26.82 km from city center
Book a stay at this golf hotel in Waukegan. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean ...
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.
Mon, May 11 - Wed, May 13
PHL
Philadelphia Intl.
MKE
General Mitchell Intl.
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Tue, Jun 2 - Tue, Jun 9
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$219 Roundtrip, found 22 hours ago
$219
Roundtrip
found 22 hours ago
Tue, Jun 2 - Tue, Jun 9
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$219 Roundtrip, found 22 hours ago
$219
Roundtrip
found 22 hours ago
Tue, Jun 2 - Tue, Jun 9
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$257 Roundtrip, found 22 hours ago
$257
Roundtrip
found 22 hours ago
Tue, Jun 2 - Tue, Jun 9
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$264 Roundtrip, found 22 hours ago
$264
Roundtrip
found 22 hours ago