Bristol Vacations
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Bristol Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Blackstone, Autograph Collection
Downtown Chicago
Price was $968, price is now $765 per person
$765
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,375, price is now $939 per person
$939
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
New York (LGA) 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.
Price to high for the quality.
Reviewed on Nov 9, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,222, price is now $893 per person
$893
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
New York (LGA) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,942, price is now $1,430 per person
$1,430
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) 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.
Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨
Reviewed on Nov 9, 2026
Swissotel - Chicago
Downtown Chicago
Price was $1,165, price is now $882 per person
$882
per person
Dec 24 - Dec 29
found 24 hours ago
Roundtrip flight included
New York (LGA) 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.
Park Hyatt Chicago
Downtown Chicago
Price was $1,972, price is now $1,547 per person
$1,547
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) 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
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
31.6 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 ...
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
29.36 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 ...
Grand Geneva Resort & Spa
7036 Grand Geneva Wy Lake Geneva WI
29.66 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
35.66 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
21.7 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
31.59 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
22.24 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
28.74 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 ...
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
21.1 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
22.94 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 ...
The Stella Hotel & Ballroom
5706 8th Ave Kenosha WI
18.99 km from city center
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 ...
Courtyard Chicago Waukegan Gurnee
3800 Northpoint Blvd Waukegan IL
26.6 km from city center
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 ...
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr Waukegan IL
27.84 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 ...
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.
Wed, Nov 18 - Sun, Nov 22
DEN
Denver Intl.
MKE
General Mitchell Intl.
$320 Roundtrip, found 2 days ago
$320
Roundtrip
found 2 days ago
Sat, Dec 5 - Tue, Dec 8
SEA
Seattle - Tacoma Intl.
MKE
General Mitchell Intl.
$322 Roundtrip, found 1 day ago
$322
Roundtrip
found 1 day ago
Wed, Nov 25 - Sun, Nov 29
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Tue, Dec 1 - Tue, Dec 8
SEA
Seattle - Tacoma Intl.
MKE
General Mitchell Intl.
$418 Roundtrip, found 1 day ago
$418
Roundtrip
found 1 day ago
Wed, Dec 2 - Mon, Dec 7
SEA
Seattle - Tacoma Intl.
MKE
General Mitchell Intl.
$444 Roundtrip, found 1 day ago
$444
Roundtrip
found 1 day ago