Dakota Holidays from £1,060

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 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

    Packages with flights are ATOL protected

Your Dakota Holiday

Enjoy unforgettable adventures when you book a holiday package to Dakota. Whether you're a foodie, art buff or just a traveller 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 holiday is clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.

Top Dakota Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,793, price is now £1,060 per person
£1,060
per person
20 Sept - 27 Sept
found 10 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Loved everything about it. Amazing room, view and pool!

Reviewed on 20 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 £2,456, price is now £1,537 per person
£1,537
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on 20 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,097, price is now £1,375 per person
£1,375
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Great spot, good location, nice rooms.

Reviewed on 20 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,174, price is now £1,426 per person
£1,426
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Staff were excellent, I needed to mail some parcels for a business event which they held for over a week (arrived earlier than expected!) breakfast was also excellent. Rooms were noisy, not from outside but from the other rooms. Walls must be thin and could hear conversation and the TV from both sides.

Reviewed on 20 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 £3,558, price is now £2,377 per person
£2,377
per person
8 Oct - 15 Oct
found 1 day ago
Return direct flight included
London (LHR) 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

Dakota Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rockford, IL (RFD-Greater Rockford)
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Freeport Art Museum, Famous Fossil Winery and Winneshiek Playhouse

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 £67 per night from 17 Sept to 18 Sept
£67
17 Sept - 18 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 £92 per night from 7 Sept to 8 Sept
£92
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (362 reviews)
"Nice place to stay. We didn't like that you rent out the pool so it was full of kids and families that were not staying at the hotel. We tried using the pool and hot tub but it was so loud with kids we left. One of the reason we stayed was so we could use the pool and hot tub. Kitchen lady was lovely!! ..."

Reviewed on 19 Aug 2025

AmericInn by Wyndham Monroe
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 £73 per night from 7 Sept to 8 Sept
£73
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (678 reviews)
OK
"The dirtiest hallway carpets I have ever seen in a hotel. The room itself was clean and comfortable. Breakfast was good but heavy on carbs."

Reviewed on 18 Aug 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Dakota travel package cost?
Less than you might think — from a low £1,060, in fact! By combining hotels, flights and car rentals into your own custom-built travel package, your Dakota escape is just a few clicks away.
If I'm not able to travel, can I cancel my Dakota travel package?
If your holiday plans in Dakota have changed, it's comforting to know that you can amend or cancel your booking. If you booked less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may impose fees. To find out more, check our Customer Service Portal.
How do I get a cheap travel package to Dakota?
You'll save a pile of money if you combine your hotels, car rentals and flights into a Dakota travel package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer more than 550 airlines and 1,000,000 hotels worldwide, so you'll always have plenty of variety to choose from. Eager to save even more? Add some fun activities to your package deal to unlock even bigger bargains! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Dakota holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your wallet. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that fits into your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's manageable monthly instalment plans. If paying small amounts each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: If you'd prefer to pay for your escape in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan with Klarna.

What are the top hotels in Dakota?
If this will be your first time in Dakota, book a room at Hyatt Regency Chicago or The Godfrey Hotel Chicago. Both offer friendly service and are favourites among many savvy travellers.
How far in advance should I book my Dakota holiday?
You'll be rewarded with the biggest variety and the cheapest prices by booking your holiday to Dakota early. Air carriers tend to publish tickets anywhere up to 12 months prior to departure, so start your planning as soon as possible. That being said, Expedia is committed to giving you the best deals around, so there's never a bad time to book your dream holiday!
What does an Expedia Dakota travel package include?
Rental cars, flights and hotels, or any combination of the three — the choice is yours. Whether you're visiting Dakota with the family or adventuring with your friends, there's a package to fit your style and budget. Once you've made your booking, why not add on a few tours as well?
What should I know before booking a Dakota travel package?
When you book your flights, hotels and car rentals together, you'll nab amazing discounts. Whether you're organising a wilderness getaway in a cabin or would rather stay in a cosy apartment in the city, Expedia will make it happen for less.
Can I choose my airline with a Dakota Expedia travel package?
Yes, you're in charge. We have access to over 550 partner airlines globally, so you can customize your Dakota escape according to your travel needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.