Monticello Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Monticello Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
$514
per person
Dec 24 - Dec 29
found 1 day 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.
The staff was 10/10.
Reviewed on Oct 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$751
per person
Dec 24 - Dec 29
found 1 day 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.
It was an overnight stay for my birthday. The hotel was clean and the staff was friendly.
Reviewed on Oct 16, 2026
Swissotel - Chicago
Downtown Chicago
$640
per person
Dec 24 - Dec 29
found 1 day 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.
Everyone was so nice and accommodating. The location is great. We had a great view of the river.
Reviewed on Oct 15, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$565
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Great extras
Good location
Reviewed on Oct 16, 2026
Holiday Inn Express Chicago - Magnificent Mile by IHG
Downtown Chicago
$563
per person
Dec 24 - Dec 29
found 1 day 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.
Eurostars Magnificent Mile
Downtown Chicago
$703
per person
Dec 24 - Dec 29
found 1 day 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.
Top Hotel Deals
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 ...
Best Western West Towne Suites
650 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 helpful staff ...
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 ...
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. ...
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 ...
Wyndham Garden Madison Fitchburg
2969 Cahill Main Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Super 8 by Wyndham Madison South
1602 W Beltline Hwy 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 and the clean ...
GrandStay Hotel & Suites Mount Horeb - Madison
175 Lillehammer Ln Mount Horeb WI
Book a stay at this spa hotel in Mount Horeb. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
Hyatt Place Madison / Verona
846 Liberty Drive Verona WI
Book a stay at this business-friendly hotel in Verona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Homewood Suites by Hilton Madison West
479 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 helpful staff ...
Country Inn & Suites by Radisson, Madison Southwest, WI
6275 Nesbitt Rd Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Holiday Inn Express Hotel & Suites Madison-Verona by IHG
515 W Verona Ave Verona WI
Book a stay at this business-friendly hotel in Verona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Sleep Inn & Suites Oregon - Madison
1120 Park Street Oregon WI
Book a stay at this business-friendly hotel in Oregon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Eugene Hotel
1517 11th St Monroe WI
Stay at this hotel in Monroe. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Monroe Arts Center and Minhas Craft Brewery are ...
Springhill Suites By Marriott Madison Fitchburg
6245 Limestone Lane Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Camp Randall Stadium and Alliant ...
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, Dec 2 - Sat, Dec 19
LAS
Harry Reid Intl.
MSN
Dane County Regional
$347
Roundtrip
found 11 hours ago
Wed, Dec 2 - Sat, Dec 19
LAS
Harry Reid Intl.
MSN
Dane County Regional
$361
Roundtrip
found 11 hours ago
Fri, Oct 30 - Tue, Nov 3
LAS
Harry Reid Intl.
MSN
Dane County Regional
$394
Roundtrip
found 5 days ago
Fri, Oct 30 - Tue, Nov 3
LAS
Harry Reid Intl.
MSN
Dane County Regional
$638
Roundtrip
found 5 days ago
Best points of interest in Monticello
- Cave of The Mounds National Natural Landmark Vacations
- New Glarus Brewing Company Vacations
- West Towne Mall Vacations
- Reddan Soccer Park Vacations
- Stoughton Opera House Vacations
- Swiss Historical Village Vacations
- University Ridge Golf Course Vacations
- Blue Mound State Park Vacations
- Tyrol Basin Ski & Snowboard Area Vacations
- Verona Ice Arena 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