Dakota Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Dakota Vacation
Enjoy unforgettable adventures when you book a vacation package to Dakota. Whether you're a foodie, art buff or just a traveler who loves to discover new places, there's something for everyone in this lively city. Your trip to Dakota wouldn't be complete without seeing a few major attractions, starting with Famous Fossil Winery. Your perfect Dakota vacation is clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.
Top Dakota Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,390
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
We were so excited about spending the time at Sable hotel however, when we arrived, it was the House of horrors. It was very filthy. Went to go grab an extra blanket and a butt plug fell out of it. Asked for them to please come clean the room they said housekeeping was not there and would take care of it tomorrow so we spent the first night in a filthy dirty room as they had no extra room rooms due to multiple concerts being held that weekend. My advice the location is great, but there’s other options that are more affordable.
Reviewed on Sep 14, 2026
Ready to book your vacation to Dakota?
Dakota Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
CA $152
CA $169 total
Sep 27 - Sep 28
includes taxes & fees
9/10 Wonderful! (941 reviews)
"We visited Freeport to spend some time with family. The staff was wonderful, very, very friendly and helpful. We extended our stay and they were very accommodating. The pool was freezing!!! Tried to enjoy it but it was just too cold. The room was very clean and the breakfast was good. Looking forward ..."
Reviewed on Sep 14, 2026
City Express By Marriott Freeport
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
CA $149
CA $165 total
Sep 27 - Sep 28
includes taxes & fees
Eugene Hotel
1517 11th St Monroe WI
CA $166
CA $182 total
Oct 8 - Oct 9
includes taxes & fees
9.8/10 Exceptional! (13 reviews)
"This hotel has just reopened after closing in 1981. They did a nice job rehabbing the property, yet it didn’t have the new paint smell. The one bedroom suite was a decent size and fairly comfortable. Location right downtown on the square was nice."
Reviewed on Sep 13, 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.
Frequently asked questions
How much does a Dakota vacation package cost?
You can grab a vacation package to this destination from CA $652 on Expedia. But how much your vacation to Dakota costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Dakota?
January, February and November are great times to search for cheap Dakota vacation packages. Travelling in less busy periods means you'll typically find reduced prices on flights and accommodations.
How many days is enough for Dakota?
The ideal duration for your Dakota vacation depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to hit all the major sights and discover some hidden treasures along the way.
How to find the best Dakota package deals?
Use Expedia's filters to find some great Dakota package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Dakota package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Dakota vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component individually. And you'll still get the freedom to create a personalized Dakota vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Dakota?
If you have your Dakota vacation dates confirmed, book early to bag some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Dakota?
- Choose when to travel: Check your diary and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Dakota.
- Set a budget: Factor in costs such as food, flights and transportation when calculating how much to save for your trip to Dakota. Then, select a hotel that suits your budget, whether that's an economical option or a more upscale getaway.
- Determine how many days away: Start by listing all the attractions and activities you'd like to experience in Dakota. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the ideal Dakota vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
