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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.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Aug. 11 - Aug. 15
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8/10 Very Good! (2,380 reviews)
It was booked as a suite. I assumed two rooms mean two bedrooms. It is NOT.
Reviewed on Jun. 18, 2024
W Chicago - Lakeshore
Downtown Chicago
Save 100% on your flight
per person
Aug. 24 - Aug. 31
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very Good! (1,006 reviews)
Good stay at the W, staff was very nice and organized.
Would stay there again for sure.
Reviewed on Jun. 17, 2024
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 22 - Aug. 25
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,230 reviews)
Location is amazing, super friendly staff. Will definitely be back soon
Reviewed on Jun. 17, 2024
Dakota Hotel Deals
Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69, Monroe, WI
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from Jul. 7 to Jul. 8
CA $93
CA $102 total
includes taxes & fees
Jul 7 - Jul 8
8.8/10 Excellent! (614 reviews)
"I was quite pleased"
Reviewed on Jun. 8, 2024
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive, Freeport, IL
Fully refundable
The price is CA $153 per night from Jul. 8 to Jul. 9
CA $153
CA $170 total
includes taxes & fees
Jul 8 - Jul 9
8.8/10 Excellent! (699 reviews)
"I liked that the staff was calm and friendly when there was an issue that happened. They are very clean and I will be booking again"
Reviewed on Jun. 16, 2024
Baymont by Wyndham Freeport
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jul. 7 to Jul. 8
CA $105
CA $117 total
includes taxes & fees
Jul 7 - Jul 8
8/10 Very Good! (548 reviews)
"I liked how helpful and caring LaMay was. I have a hard time walking and use a motorized wheelchair and I went outside to smoke a cigarette and I was coming in and she came out and helped by holding the doors open so I could get in easy."
Reviewed on Jun. 10, 2024
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
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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.