Rutland Trip

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Top Rutland Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was ₹50,143, price is now ₹40,232 per person
₹40,232
per person
21 Dec - 24 Dec
found 1 day ago
Return direct flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was ₹190,290, price is now ₹52,850 per person
₹52,850
per person
21 Dec - 24 Dec
found 1 day ago
Return direct flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ₹66,474, price is now ₹49,739 per person
₹49,739
per person
21 Dec - 24 Dec
found 1 day ago
Return direct flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was ₹53,914, price is now ₹42,802 per person
₹42,802
per person
21 Dec - 24 Dec
found 1 day ago
Return direct flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
Excellent experience. Thank you.

Reviewed on 31 Oct 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₹51,260, price is now ₹41,300 per person
₹41,300
per person
21 Dec - 24 Dec
found 1 day ago
Return direct flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
Good stay, has the basics for sleeping after a night out. Small but adequate

Reviewed on 31 Oct 2026

Top hotels in Rutland

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is ₹11,219 per night from 8 Nov to 9 Nov
₹11,219
₹12,959 total
8 Nov - 9 Nov
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Fully refundable
The price is ₹4,177 per night from 15 Nov to 16 Nov
₹4,177
₹4,825 total
15 Nov - 16 Nov
includes taxes & fees
6.2/10 (1,059 reviews)
"They sold my room after I had booked it with Expedia and had my confirmation number. And when I called the staff was very rude and disrespectful"

Reviewed on 28 Oct 2026

Motel 6 Madison, WI - East
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

3 out of 5
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is ₹6,296 per night from 2 Dec to 3 Dec
₹6,296
₹7,271 total
2 Dec - 3 Dec
includes taxes & fees
9/10 Wonderful! (1,389 reviews)
"A very nice family hotel. Clean rooms. Good night's sleep. Good breakfast. Good hot tub & pool. Great staff."

Reviewed on 31 Oct 2026

AmericInn by Wyndham Madison West
See all 403 properties in Rutland
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 does a Rutland holiday package cost?
You'll find cheap prices from ₹40,232 on Expedia for your Rutland break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your holiday to Rutland costs.
What are the cheapest months to go to Rutland?
January, February and November are great times to search for cheap Rutland holiday packages. Choosing to travel in less busy periods means you'll typically find lower prices on flights and accommodation.
How many days is enough for Rutland?
The ideal duration of your Rutland holiday depends on what you'd like to do. Typically, a few days to a week will give you enough time to tick off all the top sights and discover some hidden treasures along the way.
How to find the best Rutland package deals?
Start your search for a Rutland package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Rutland package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Rutland getaway off to a flying start.
Is it cheaper to book a Rutland holiday as a package?
You can enjoy significant savings on your Rutland retreat by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to browse some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Rutland?
If you have your Rutland travel dates confirmed, book early to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Rutland?

  1. Choose when to go: Check your diary and pack your bags. Your favourite time of year and the activities available will also help you decide when to holiday in Rutland.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and meals to activities and airfares. Your accommodation will probably be the largest expense during your trip to Rutland.
  3. Decide how long to go for: Now that you're more familiar with Rutland, you can work out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your accommodation and airfare: Once you've settled on your trip dates and duration, book the perfect Rutland holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.