Dakota Vacations from $453
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Dakota Vacation Packages
- Sheraton Grand Chicago Riverwalk
Dec 20 - Dec 23Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago3 nights4.0 star property8.6/10 - Excellent (1,880 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago Fulton Market
Jan 23 - Jan 27Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (608 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$911$575found 1 day agoper traveler - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jan 23 - Jan 27Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago4 nights4.0 star property9.4/10 - Exceptional (2,782 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$1,563$1,078found 1 day agoper traveler - The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Dec 25 - Dec 30The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago + Flight
Downtown Chicago5 nights4.5 star property9.6/10 - Exceptional (1,000 reviews)"The hotel lobby and rooftop are nice but the rooms are okay. We had 3 rooms and the shower pressure was terrible in all. The king room felt small so we switched to 2 queens which was much better. The service was so good though and it’s attached to a mall. It was good overall but probably won’t stay here again."Reviewed October 29, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$1,250$883found 1 day agoper traveler - The Emily Hotel
Jan 23 - Jan 27The Emily Hotel + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (1,357 reviews)"The location of this hotel is great with the exception of its proximity to the train tracks. There were train horns sounding at all hours and fairly frequently. The hot water in my room took an extremely long time and house keeping didn’t always replenish/ replace items they would remove such as dark face cloth for makeup removal and wet makeup removal towelette."Reviewed November 10, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$1,101$779found 1 day agoper traveler
Dakota Hotel Deals
"Great one-night stay. Friendly staff and a clean, spacious room. We missed breakfast because we overslept."
City Express By Marriott Freeport
City Express By Marriott Freeport
Country Inn & Suites by Radisson, Freeport, IL
Country Inn & Suites by Radisson, Freeport, IL
"Enjoyed the custom made omelet. Friendly staff. Hot tub was wonderful."
"Beautiful hotel great location"
"We stayed for 5 nights and were very pleased! They had great housekeeping services, maintenance was there and was helpful when it came to the pool which my kids loved! We had a great stay! Quiet, respectful people who had dogs and we didn’t even know!! Washer and dryer were easy to use! And breakfast included was great!! My kids loved the waffles and bagels! Definitely would stay again!!"
Frequently Asked Questions
How much does a Dakota vacation package cost?
You can grab a vacation package to this destination from $453 on Expedia. However, how much your vacation to Dakota costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Dakota?
You can typically find lower rates and greater availability in August, September and December. Take a look at our cheap Dakota vacation packages and you could score some great off-season discounts.
How many days is enough for Dakota?
With a well-planned itinerary, you can easily tick off the main Dakota sights in a handful of days. But if you'd like to discover hidden spots or go on day trips, consider booking your Dakota vacation for longer.
How to find the best Dakota package deals?
Bagging a cheap Dakota package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Dakota package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Dakota vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and stays separately. Better still, you can personalize your Dakota trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Dakota?
If you've got your Dakota vacation dates finalized, book as soon as you can to bag some awesome deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Dakota vacation packages?
Your Dakota getaway should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.