Bristol Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Bristol Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
$549
per person
Dec 24 - Dec 29
found 8 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,744
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$797
per person
Dec 24 - Dec 29
found 8 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.
Breakfast wasn’t good, everything was very either old and stale and the cups smelled like breath . Overall stay was amazing just do better with breakfast
Reviewed on Oct 19, 2026
Swissotel - Chicago
Downtown Chicago
$693
per person
Dec 24 - Dec 29
found 8 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.
I found a parking spot in 303 wacker. The building next door off of spothero for 18 dollars a day. It’s tough to get to because it’s on lower Columbus but you come out right next door to the hotel
Reviewed on Oct 19, 2026
Sheraton Grand Chicago Riverwalk
Downtown Chicago
$978
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
It took 55 minutes to check in and then when I was taking a shower, the showerhead fell off and the water pressure almost knocked me down, and you had to wiggle the toilet to get us to stop
Reviewed on Oct 19, 2026
Holiday Inn Express Chicago - Magnificent Mile by IHG
Downtown Chicago
$607
per person
Dec 24 - Dec 29
found 8 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 a fitness center. Our guests praise the breakfast and 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
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
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
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
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 ...
The Cove Of Lake Geneva
111 Center St Lake Geneva WI
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 ...
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
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 Inn on Sheridan
2723 Sheridan Rd Zion IL
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
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 ...
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
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 ...
Country Inn & Suites by Radisson Kenosha - Pleasant Prairie
7011 122nd Ave Kenosha WI
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 ...
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
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. ...
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr Waukegan IL
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 ...
Hampton Inn Chicago - Gurnee
5550 Grand Ave Gurnee IL
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 Great Lakes Naval Base
3000 North Skokie Highway North Chicago IL
Book a stay at this business-friendly hotel in North Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Hotel Indigo Chicago-Vernon Hills by IHG
450 N Milwaukee Ave Vernon Hills IL
Book a stay at this boutique hotel in Vernon Hills. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
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, Nov 26 - Thu, Dec 3
DEN
Denver Intl.
MKE
General Mitchell Intl.
$257
Roundtrip
found 5 days ago
Sat, Nov 21 - Wed, Nov 25
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$285
Roundtrip
found 14 hours ago
Tue, Nov 24 - Wed, Dec 2
DEN
Denver Intl.
MKE
General Mitchell Intl.
$357
Roundtrip
found 5 days ago
Tue, Nov 24 - Wed, Dec 2
SEA
Seattle - Tacoma Intl.
MKE
General Mitchell Intl.
$377
Roundtrip
found 2 days ago
Mon, Nov 23 - Mon, Dec 7
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$385
Roundtrip
found 3 days ago
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