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.
Swissotel - Chicago
Downtown Chicago
Price was $766, price is now $592 per person
$592
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) 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.
This place is great and clean
Reviewed on Oct 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,056, price is now $697 per person
$697
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,768, price is now $1,330 per person
$1,330
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The best of the best. The largest rooms in town at the very best price with the very best experience.
Reviewed on Oct 26, 2026
Pendry Chicago
Downtown Chicago
Price was $1,149, price is now $869 per person
$869
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Talbott, Autograph Collection
Downtown Chicago
Price was $837, price is now $641 per person
$641
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) 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.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,808, price is now $1,393 per person
$1,393
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Hotel Deals
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 ...
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 2 restaurants. Our guests praise the pool and the helpful staff ...
Grand Geneva Resort & Spa
7036 Grand Geneva Wy Lake Geneva WI
25.68 km from city center
Book a stay at this spa resort in Lake Geneva. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
32.15 km from city center
Book a stay at this business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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 ...
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 ...
The Inn on Sheridan
2723 Sheridan Rd Zion IL
25.38 km from city center
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 ...
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 ...
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr Waukegan IL
27.18 km from city center
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 ...
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. ...
Americas Best Value Inn & Suites Racine
5419 Durand Ave Mount Pleasant WI
30.53 km from city center
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 ...
Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant
13340 Hospitality Ct Mount Pleasant WI
27.25 km from city center
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
15.2 km from city center
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 ...
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 4 days ago
$211
Roundtrip
found 4 days ago
Thu, Nov 26 - Wed, Dec 2
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$265 Roundtrip, found 4 days ago
$265
Roundtrip
found 4 days ago
Fri, Nov 27 - Tue, Dec 1
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$268 Roundtrip, found 4 days ago
$268
Roundtrip
found 4 days ago
Fri, Nov 27 - Tue, Dec 1
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$279 Roundtrip, found 4 days ago
$279
Roundtrip
found 4 days ago
Wed, Nov 25 - Sun, Nov 29
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$324 Roundtrip, found 4 days ago
$324
Roundtrip
found 4 days ago