Dakota Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

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

Dakota Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was S$3,839, price is now S$2,719 per person
S$2,719
per person
9 Oct - 15 Oct
found 23 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Check in and out was seamless! Got excellent help with bags and access to amenities! Great location it was about a 9 min walk to Riverwalk, Hop on Bus; felt safe and area was clean

Reviewed on 18 Aug, 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$4,369, price is now S$2,983 per person
S$2,983
per person
9 Oct - 15 Oct
found 23 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Loved the hotel. Very clean and comfortable. The gentleman who checked us out was not the most friendly, but everyone else was super helpful!

Reviewed on 18 Aug, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$4,258, price is now S$2,932 per person
S$2,932
per person
9 Oct - 15 Oct
found 23 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
My family and I love this place

Reviewed on 19 Aug, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$5,300, price is now S$3,680 per person
S$3,680
per person
9 Oct - 15 Oct
found 23 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$3,827, price is now S$2,741 per person
S$2,741
per person
9 Oct - 15 Oct
found 23 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Terrible mattresses, old and crunchy or something; bad lumpy pillows. No coffee or water in the room. If you want free coffee, you gotta track to the lobby during coffee hours and pay a "resort" fee for the experience.

Reviewed on 17 Aug, 2025

Top hotels in Dakota

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 S$117 per night from 17 Sept to 18 Sept
S$117
17 Sept - 18 Sept
includes taxes & fees
6.8/10 (334 reviews)
"Local"

Reviewed on 16 Aug, 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 S$133 per night from 17 Sept to 18 Sept
S$133
17 Sept - 18 Sept
includes taxes & fees
8/10 Very Good! (676 reviews)
"Property was clean and close to highway."

Reviewed on 1 Aug, 2025

Baymont by Wyndham Freeport
Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

2.5 out of 5
1710 South Dirck Drive, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is S$160 per night from 7 Sept to 8 Sept
S$160
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (803 reviews)
"this hotel is the best to offer in this city"

Reviewed on 13 Aug, 2025

Country Inn & Suites by Radisson, Freeport, IL
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 S$2,719 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.