Deals on vacations and trips to Monticello

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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,427, price is now $835 per person
$835
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,339, price is now $1,368 per person
$1,368
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,627, price is now $958 per person
$958
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,530, price is now $916 per person
$916
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,579, price is now $953 per person
$953
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

Top Monticello hotels deals

Jaggi Swiss Gasthaus

Jaggi Swiss Gasthaus

Monticello WI
Get rates
Stay at this B&B in Monticello. Enjoy private pools, patios, and an in-room coffeemaker. Popular attractions New Glarus Woods State Park and New Glarus Woods State Park Trailhead are located nearby.
Pool
Air conditioning
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

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

Monticello WI
Get rates
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
483 Commerce Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $83 total per night
$83 total
Jan 23 - Jan 24, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Tru by Hilton Madison West, WI

Tru by Hilton Madison West, WI

2.5 out of 5
8102 Watts Rd. Madison WI
Free Cancellation
Reserve now, pay when you stay
$65 nightly
The price is $75 total per night
$75 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Breakfast included
Pet friendly
Baymont Inn & Suites by Wyndham Madison

Baymont Inn & Suites by Wyndham Madison

2.5 out of 5
2810 Coho Street Madison WI
Free Cancellation
Reserve now, pay when you stay
$55 nightly
The price is $64 total per night
$64 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Relax with a drink at the bar/lounge and enjoy free perks like full breakfast and free self parking. A business center, free WiFi in public areas, and a lobby fireplace are also on offer.
Pool
Breakfast included
Homewood Suites by Hilton Madison West

Homewood Suites by Hilton Madison West

3 out of 5
479 Commerce Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $103 total per night
$103 total
Dec 26 - Dec 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
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See all available properties in Monticello
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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.

Frequently asked questions

How much are vacation packages to Monticello?
With Travelocity vacation packages, you could be living it up in Monticello from just $835. Activities, flights and hotels — we have it all. You can save some cash just by combining your bookings together. With everything taken care of before you go, you won't have a care in the world.
Where can I get the best vacation package deals for Monticello?
You can score terrific Monticello package deals with Travelocity. Mix and match from as many as 400 air carriers and 1,000,000 worldwide properties and turn those vacation daydreams into reality.
Why should I book my Monticello vacation bundle with Travelocity?
Travel should be about making fantastic new memories and leaving all your worries behind — which is why we provide you with a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our superb range of vacation packages. So what are you waiting for? There's no time like the present to secure the vacation of a lifetime.
Will I save money on my Monticello car rental if I book it with a hotel or flight?
Bundling your car, flight and hotel into a Monticello vacation package is an easy way to land the best prices. Plus, having your own wheels gives you the freedom to make your way to all those famous sights you're hoping to check out. Located 110 mi from Monticello, Wrigley Field is one place that should feature on your itinerary. Load up the car and make a day trip of it.
Which airport is best for Monticello?
There's a good chance you'll land at Dane County Regional Airport (MSN), situated 30 mi northeast of inner Monticello. Rockford, IL (RFD-Greater Rockford) (45 mi away from central Monticello) and Dubuque Regional Airport (DBQ) (60 mi away from central Monticello) are other options.
Where should I stay when visiting Monticello?
If you're looking for somewhere to lay your head, consider the Jaggi Swiss Gasthaus. It's the top pick for many visitors.

Photos of local treasures

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