Dakota Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Beautiful hotel , breakfast was amazing

Reviewed on Jul. 30, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Loved the bar/restaurant and rooftop bar

Reviewed on Jul. 30, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Wonderful hotel in a great location along the river. The view from Terrace 16 is amazing! Also, the pillows on the bed are really comfortable. I love this hotel and would recommend it to anyone.

Reviewed on Jul. 30, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
Finding a park is hard and the process of getting a room is very tedious but still very beautiful I’ve been twice

Reviewed on Jul. 29, 2025

Ready to book your vacation to Dakota?

 

Choose your dates

Dakota Hotel Deals

AmericInn by Wyndham Monroe

AmericInn by Wyndham Monroe

2.5 out of 5
424 4th Ave, Monroe, WI
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Aug 17 to Aug 18
CA $171
CA $187 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (359 reviews)
Noisy beds
"Excellent hotel however, the beds make a horrific noise when you touch the base of them. It wakes everyone in the room, even if you’re trying to be quiet very concerning you should replace or baffle the bottom of the bed."

Reviewed on Jul. 27, 2025

AmericInn by Wyndham Monroe
Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Aug 3 to Aug 4
CA $113
CA $125 total
Aug 3 - Aug 4
includes taxes & fees
6.8/10 (331 reviews)
nicer than I expected
"I didnt go in expecting a lot, but the hotel was way nicer than I thought. Always thought "super 8" was just a cheap place, some might be, but this one was nice"

Reviewed on Jul. 17, 2025

Super 8 by Wyndham Freeport
Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

2.5 out of 5
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Aug 10 to Aug 11
CA $132
CA $147 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (672 reviews)
Good option in area
"Very nice Staff… Property a little rundown was the only reason I marked down one star. I would stay here again."

Reviewed on Jul. 26, 2025

Baymont by Wyndham Freeport
See all 34 properties in Dakota
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Dakota vacation package cost?
You can grab a vacation package to this destination from CA $713 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.