Dakota Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Dakota

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €945, price is now €629 per person
€629
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on 26 Aug 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,207, price is now €796 per person
€796
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Very nice hotel and staff were pleasant. The area is okay but if you go a block over it is nicer. The river walk is very close and inviting.

Reviewed on 25 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,010, price is now €680 per person
€680
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (339 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was €2,292, price is now €1,578 per person
€1,578
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Great location but a busy area

Reviewed on 25 Aug 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Price was €1,165, price is now €816 per person
€816
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (1,872 reviews)
Hotel staff went above and beyond to make our stay great, even upgraded our room to a larger one for no extra charge!

Reviewed on 26 Aug 2025

Top hotels in Dakota

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 €84 per night from 7 Sept to 8 Sept
€84
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (679 reviews)
"Staff and service were great. Carpet and walls/trim on all floors were dirty and peeling. Overall a good stay."

Reviewed on 20 Aug 2025

Baymont by Wyndham Freeport
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 €72 per night from 21 Sept to 22 Sept
€72
21 Sept - 22 Sept
includes taxes & fees
6.8/10 (334 reviews)
"Local"

Reviewed on 16 Aug 2025

Super 8 by Wyndham Freeport
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 €104 per night from 21 Sept to 22 Sept
€104
21 Sept - 22 Sept
includes taxes & fees
AmericInn by Wyndham Monroe
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.

Frequently asked questions

How much does a Dakota holiday package cost?
You can grab a holiday package to this destination from €629 on Expedia. However, how much your holiday 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 usually find reduced prices and better availability in January, February and November. Explore our cheap Dakota holiday packages and you could score some great off-season discounts.
How many days is enough for Dakota?
The ideal length of your Dakota holiday depends on what you'd like to see and do. Usually, a handful of days to a week will give you time to visit all the main attractions and discover some hidden spots along the way.
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 customise 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 holiday as a package?
An Expedia holiday package could land you great savings when compared to booking flights and stays separately. Better still, you can personalise 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 holiday package to Dakota?
If you've got your Dakota holiday 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.
How to plan a trip to Dakota?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Dakota.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and experiences. Your hotel will likely be the biggest expense during your trip to Dakota.
  3. Decide how long to go away for: Now that you know more about Dakota, you can figure out the perfect length of your break. Put together a rough plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customised Dakota holiday package.

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