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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$499
per person
Dec 17 - Dec 21
found 21 hours ago
Roundtrip non-stop flight included
Columbia (CAE) 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.
Swissotel - Chicago
Downtown Chicago
$684
per person
Dec 17 - Dec 21
found 21 hours ago
Roundtrip non-stop flight included
Columbia (CAE) 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$604
per person
Dec 17 - Dec 21
found 21 hours ago
Roundtrip non-stop flight included
Columbia (CAE) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,221
per person
Dec 17 - Dec 21
found 21 hours ago
Roundtrip non-stop flight included
Columbia (CAE) 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.
Level Chicago - River North
Downtown Chicago
$764
per person
Dec 17 - Dec 21
found 21 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Outstanding room. I highly recommend. Be sure to check out the 6th floor and all the amenities!
Reviewed on Sep 23, 2026
Park Hyatt Chicago
Downtown Chicago
$1,186
per person
Dec 17 - Dec 21
found 21 hours ago
Roundtrip non-stop flight included
Columbia (CAE) 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 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 ...
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. ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
MainStay Suites Fitchburg - Madison
5421 Caddis Bnd 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 ...
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 ...
Sleep Inn & Suites Verona - Madison Southwest
131 Horizon Drive Verona WI
Stay at this hotel in Verona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Verona ...
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 ...
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. ...
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 Ten Pin ...
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, Oct 26 - Sun, Nov 1
DEN
Denver Intl.
MSN
Dane County Regional
$339
Roundtrip
found 6 days ago
Mon, Oct 26 - Sun, Nov 1
DEN
Denver Intl.
MSN
Dane County Regional
$341
Roundtrip
found 6 days ago
Sat, Dec 26 - Tue, Jan 5
BOS
Logan Intl.
MSN
Dane County Regional
$383
Roundtrip
found 1 day ago
Tue, Oct 6 - Tue, Oct 20
PDX
Portland Intl.
MSN
Dane County Regional
$611
Roundtrip
found 5 days ago
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