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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$743
per person
Nov 20 - Nov 26
found 4 hours ago
Roundtrip flight included
Des Moines (DSM) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$786
per person
Nov 20 - Nov 26
found 4 hours ago
Roundtrip flight included
Des Moines (DSM) 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.
Eurostars Magnificent Mile
Downtown Chicago
$809
per person
Nov 20 - Nov 26
found 4 hours ago
Roundtrip flight included
Des Moines (DSM) 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.
Arlo Chicago
Downtown Chicago
$773
per person
Nov 20 - Nov 26
found 4 hours ago
Roundtrip flight included
Des Moines (DSM) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Arlo Hotel is 5 stars from the location to the rooms ,staff, cleanliness, and probably the most comfortable beds that I have ever slept on in a hotel room. Nice bar for a good meal and drinks without even leaving the property .Will definitely book at the Arlo hotel when in Chicago for future visits.
Reviewed on Sep 20, 2026
The Emily Hotel
Downtown Chicago
$917
per person
Nov 20 - Nov 26
found 4 hours ago
Roundtrip flight included
Des Moines (DSM) to Chicago (ORD)
Book a stay at this business-friendly 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 United Center and Chicago Riverwalk are located nearby.
Silversmith Hotel Chicago Downtown
Downtown Chicago
$820
per person
Nov 20 - Nov 26
found 4 hours ago
Roundtrip flight included
Des Moines (DSM) to Chicago (ORD)
Book a stay at this business-friendly 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 Millennium Park and Chicago Riverwalk are located nearby.
Great staff but unnecessary fees
Reviewed on Sep 20, 2026
Top Hotel Deals
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 ...
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 ...
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 ...
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. ...
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 ...
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 ...
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 ...
Holiday Inn Club Vacations at Lake Geneva Resort by IHG
7036 Grand Geneva Way Lake Geneva WI
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. ...
Red Roof Inn Gurnee - Waukegan
3031 Belvidere Rd Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
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 ...
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 ...
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 ...
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road Grayslake IL
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 ...
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.
Tue, Nov 17 - Thu, Nov 26
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$198
Roundtrip
found 1 day ago
Tue, Nov 17 - Thu, Nov 26
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$237
Roundtrip
found 1 day ago
Tue, Nov 17 - Thu, Nov 26
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$282
Roundtrip
found 1 day ago
Tue, Nov 17 - Thu, Nov 26
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$282
Roundtrip
found 1 day ago
Tue, Nov 17 - Thu, Nov 26
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$283
Roundtrip
found 1 day ago
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