
Dakota Vacations from $169
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Your Dakota Vacation
Enjoy unforgettable adventures when you book a vacation package to Dakota. Whether you're a foodie, art buff or just a traveler 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 vacation is clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.
The Latest Dakota vacation packages
Price found within the past 48 hours. Click for updated prices.

Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $273, price is now $169 per person
$169
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Room was wonderful and clean!
Reviewed on Dec 6, 2025

The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $665, price is now $394 per person
$394
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Nov 26, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $828, price is now $496 per person
$496
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on Dec 2, 2025

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $630, price is now $383 per person
$383
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views.
Reviewed on Dec 3, 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
Price was $538, price is now $337 per person
$337
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
The Chicago Athletic Association Hotel is the most charming hotel in the city of Chicago. My wife and I recently got married in Chicago and one of the highlights of the weekend was hanging out at the hotel! It has a roaring 20's vibe with the dark woods in the main lobby and the large game room which is a fun place to get a drink and play chess/pool. Amazing location close to the Amtrak, Chicago subway, and the South shore railroad. And it's across the street from Millennium Park. Most importantly, the staff is very professional and attentive and will go above and beyond to make your stay perfect. I always stay at this hotel when I go to Chicago because of it's charm and service. I would never stay anywhere else because it's a truly unique hotel in an awesome location with the nicest and most professional staff. 10/10 recommend to anyone!
Reviewed on Nov 20, 2025
Dakota Hotel Deals

Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
$103 nightly
The price is $114 total per night from Jan 4 to Jan 5
$114 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (843 reviews)
Room was clean. Staff friendly and helpful. No problems.
Reviewed on Nov 22, 2025

Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $74 total per night from Dec 15 to Dec 16
$74 total
Dec 15 - Dec 16
Total with taxes and fees
8.8/10 Excellent! (798 reviews)
Welcome staff was excellent
Reviewed on Nov 29, 2025

Baymont by Wyndham Freeport
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $87 total per night from Jan 4 to Jan 5
$87 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
7.8/10 Good! (709 reviews)
Stayed for a night, i must say the stay is nice. The place needs updating. Not today but in the future.
Reviewed on Nov 28, 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.
Find the Best Dakota Vacation Packages
Dakota Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rockford, IL (RFD-Greater Rockford) |
Top Sights | Freeport Art Museum, Famous Fossil Winery and Silver Creek Museum |
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