
Monticello Vacation Packages
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Your Monticello Vacation
Amazing adventures await when you book a Monticello vacation package. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this vibrant city. New Glarus Brewing Company, Swiss Historical Village and Swissland Miniature Golf are just a few of the many sights worth visiting during your trip to Monticello. Don't delay your visit to this city any longer. The perfect Monticello vacation is a couple of clicks away with Expedia.
Top Monticello Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Price was CA $1,146, price is now CA $815 per person
CA $815
per person
Sep 16 - Sep 18
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (622 reviews)
This hotel is very new and clean. It has a brand new shopping area with restaurants right across the parking lot. It’s a perfect place to stay for a night or two. Easy access to the train and taxis/Ubers are readily available to get to the heart of downtown.
Reviewed on Jun 19, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,809, price is now CA $1,248 per person
CA $1,248
per person
Aug 26 - Aug 29
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026

Pendry Chicago
Downtown Chicago
Price was CA $1,863, price is now CA $1,320 per person
CA $1,320
per person
Sep 3 - Sep 6
found 3 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!
Reviewed on Jun 18, 2026

The Emily Hotel
Downtown Chicago
Price was CA $1,918, price is now CA $1,396 per person
CA $1,396
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Close to a ton of great dining options. Nice staff
Reviewed on Jun 20, 2026
Monticello Hotel Deals

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Monticello WI

Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Jun 21 to Jun 22
CA $118
CA $136 total
Jun 21 - Jun 22
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"El piso estaba pegajoso"
Reviewed on Jun 20, 2026

AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Jun 29 to Jun 30
CA $104
CA $120 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (1,207 reviews)
"It’s close to restaurants and shopping"
Reviewed on Jun 19, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







