Dakota Holidays from £934

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

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

  • 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 £1,506, price is now £934 per person
£934
per person
5 Sept - 10 Sept
found 3 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Holes in the carpeting in living room. Door that enters unit doesn’t close without slamming it. Looks like wear and tear since we were there before.

Reviewed on 14 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,433, price is now £948 per person
£948
per person
5 Sept - 10 Sept
found 3 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows. In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week. Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).

Reviewed on 14 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,977, price is now £1,349 per person
£1,349
per person
5 Sept - 10 Sept
found 3 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk. It took us a little while to figure out all the lighting but that was a small thing. The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good! All in all, a very happy experience.

Reviewed on 14 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,403, price is now £980 per person
£980
per person
5 Sept - 10 Sept
found 3 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Free beer no perfect everyone was great

Reviewed on 15 Jul 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,212, price is now £1,594 per person
£1,594
per person
8 Oct - 13 Oct
found 7 hours ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was friendly and helpful. Great value for price we paid.

Reviewed on 15 Jul 2026

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

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 refundable
The price is £105 per night from 19 Jul to 20 Jul
£105
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (914 reviews)
"Staff was very pleasant and helpful"

Reviewed on 13 Jul 2026

Country Inn & Suites by Radisson, Freeport, IL
City Express By Marriott Freeport

City Express By Marriott Freeport

3 out of 5
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
The price is £89 per night from 22 Jul to 23 Jul
£89
22 Jul - 23 Jul
includes taxes & fees
8/10 Very good! (751 reviews)
"Staff was friendly, room was clean, slow draining in sink, shower pressure was okay, tv channels unavailable no offer of compensation."

Reviewed on 7 Jul 2026

City Express By Marriott Freeport
Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

2 out of 5
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is £73 per night from 11 Aug to 12 Aug
£73
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (878 reviews)
"Good location and overall property is a great value."

Reviewed on 3 Jul 2026

Super 8 by Wyndham Monroe WI
See all 39 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 £934, 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.

Explore a world of travel with Expedia

* 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.