Belleville Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Belleville 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
just found
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
just found
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.
Great property!! Beautiful rooftop bar!!
Reviewed on Oct 19, 2026
The Talbott, Autograph Collection
Downtown Chicago
$807
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, 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.
Clean room. Valet service slow.
Reviewed on Oct 18, 2026
Swissotel - Chicago
Downtown Chicago
$693
per person
Dec 24 - Dec 29
just found
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
Top Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
Stay at this motel in Madison. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Edgewater
1001 Wisconsin Place Madison WI
Book a stay at this luxury hotel in Madison. Enjoy a full-service spa, 4 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Valued Stay Madison
6606 Maahic Way Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
DoubleTree by Hilton Madison Downtown
525 West Johnson Street Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the breakfast and the ...
Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
La Quinta Inn & Suites by Wyndham Madison American Center
5217 E Terrace Dr Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
The Dylin
611 E Dayton St Madison WI
Stay at this aparthotel in Madison. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Camp Randall Stadium and Alliant ...
Cambria Hotel Madison East
5045 Eastpark Blvd Madison WI
Book a stay at this family-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Days Inn & Suites by Wyndham Madison
4402 E Broadway Srvcs Rd Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hampton Inn & Suites Madison-West
483 Commerce Dr Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Baymont Inn & Suites by Wyndham Madison
2810 Coho Street Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Sat, Oct 24 - Tue, Oct 27
DEN
Denver Intl.
MSN
Dane County Regional
$257
Roundtrip
found 2 days ago
Thu, Nov 26 - Wed, Dec 2
DEN
Denver Intl.
MSN
Dane County Regional
$349
Roundtrip
found 1 day ago
Tue, Nov 17 - Sun, Dec 6
LAS
Harry Reid Intl.
MSN
Dane County Regional
$353
Roundtrip
found 1 day ago
Fri, Oct 30 - Tue, Nov 3
LAS
Harry Reid Intl.
MSN
Dane County Regional
$658
Roundtrip
found 17 hours ago
Best points of interest in Belleville
- University of Wisconsin-Madison Vacations
- Alliant Energy Center Vacations
- Camp Randall Stadium Vacations
- East Towne Mall Vacations
- Wisconsin State Capitol Vacations
- University of Wisconsin Hospital and Clinics Vacations
- Kohl Center Vacations
- Monona Terrace Community and Convention Center Vacations
- Capitol Square Vacations
- Ho-Chunk Gaming Madison Vacations
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