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 Emily Hotel
Downtown Chicago
$652
per person
Dec 22 - Dec 28
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$1,437
per person
Nov 6 - Nov 13
found 9 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
This was my first stay at a Hotel Riu and I was thoroughly impressed! It reminded me of the hotels in Southeast Asia I have visited - attentive staff, very clean facilities, attention to details, and the best breakfast buffet I have probably ever had at a US hotel that is included in the hotel room rate. The bonus to all of this being that it was literally steps from the Magnificent Mile and had easy access to Express bus lines and the MTA. Would definitely stay here again!
Reviewed on Oct 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,304
per person
Nov 6 - Nov 10
found 6 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
Hands down the best hotel in Chicago!
Reviewed on Oct 5, 2026
Level Chicago – Old Town
Downtown Chicago
$1,418
per person
Nov 6 - Nov 13
found 9 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
I had booked an Executive Room months in advanced and when I got there they gave me a much smaller room then I was expecting
Reviewed on Oct 4, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$844
per person
Nov 6 - Nov 13
found 9 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
The Talbott, Autograph Collection
Downtown Chicago
$1,256
per person
Nov 6 - Nov 13
found 9 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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, Nov 23 - Thu, Nov 26
SEA
Seattle - Tacoma Intl.
MKE
General Mitchell Intl.
$200
Roundtrip
found 16 hours ago
Sat, Oct 17 - Tue, Oct 27
DEN
Denver Intl.
MKE
General Mitchell Intl.
$309
Roundtrip
found 3 days ago
Thu, Nov 5 - Sat, Nov 21
TPA
Tampa Intl.
MKE
General Mitchell Intl.
$373
Roundtrip
found 1 day ago
Fri, Oct 23 - Tue, Oct 27
DEN
Denver Intl.
MKE
General Mitchell Intl.
$383
Roundtrip
found 3 days ago
Tue, Nov 24 - Sat, Dec 5
LAX
Los Angeles Intl.
MKE
General Mitchell Intl.
$391
Roundtrip
found 19 hours ago
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations