Dakota Holidays from AU$4,525
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$703 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Dakota Holiday
The adventure-filled city of Dakota is calling your name. Discover its hot spots and hidden treasures with a Dakota holiday package that's customised to you. Your trip to Dakota wouldn't be complete without swinging by its top attractions, such as Famous Fossil Winery. Expedia can help you escape your daily routine. Tailor your holiday to Dakota to suit your style of travel, whatever that may be!
The Latest Dakota Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was AU$5,213, price is now AU$4,525 per person
AU$4,525
per person
5 Jan - 12 Jan
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
I thoroughly enjoyed my time at Pendry Chicago. I stayed in a tower king room. I originally was going to stay in a suite but the normal king room was very spacious for one person. The valet service was pretty quick and the valets were all very nice. The front desk clerk was extremely helpful and professional. I loved staying right on Michigan Ave and within walking distance to so many things. I read some reviews saying safety was a concern but I didn’t experience any safety issues. They lock the doors on Michigan Ave after a certain point to keep the flow of traffic thru a better monitored entrance. I also took an evening(beginning around 9:30pm) stroll around Millennium Park, down to Buckingham fountain and back up Michigan Ave to the river and the surroundings blocks around the hotel. At no point did I feel unsafe and would highly recommend this hotel to anyone coming to Chicago. The location is fantastic, the employees are amazing and the rooms are comfy. What more could you ask for?
Reviewed on 26 Nov 2025
Chicago luxury home suites
Downtown Chicago
Price was AU$10,180, price is now AU$8,005 per person
AU$8,005
per person
5 Jan - 12 Jan
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on 26 Nov 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was AU$6,610, price is now AU$5,352 per person
AU$5,352
per person
5 Jan - 12 Jan
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great stay. Excellent location.
Reviewed on 23 Nov 2025
The Emily Hotel
Downtown Chicago
Price was AU$5,866, price is now AU$4,902 per person
AU$4,902
per person
5 Jan - 12 Jan
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on 26 Nov 2025
The Peninsula Chicago
Downtown Chicago
Price was AU$7,272, price is now AU$6,190 per person
AU$6,190
per person
5 Jan - 12 Jan
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room is great and service has been exceptional!!
Reviewed on 24 Nov 2025
Dakota Holiday
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 | Winneshiek Playhouse, Famous Fossil Winery and Freeport Art Museum |
Our pick of the best Dakota Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is AU$187 per night from 28 Dec to 29 Dec
AU$187
28 Dec - 29 Dec
includes taxes & fees
8.8/10 Excellent! (842 reviews)
Great staff.
Reviewed on 13 Nov 2025
AmericInn by Wyndham Monroe
424 4th Ave Monroe WI
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 25 Dec to 26 Dec
AU$191
25 Dec - 26 Dec
includes taxes & fees
8.6/10 Excellent! (377 reviews)
Would stay again!
Reviewed on 26 Oct 2025
Baymont by Wyndham Freeport
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 28 Dec to 29 Dec
AU$140
28 Dec - 29 Dec
includes taxes & fees
7.8/10 Good! (706 reviews)
Had i not made my reservation ahead of time and saw the condition of the carpets first, I probably would have not checked in. If our room wasn't clean when we opened the room door, i would have left. It appears the hall/stair carpets have never been cleaned and/or vacuumed rarely. My first impression ...
Reviewed on 1 Nov 2025
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.
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.
