Flights To Dickinson County - Cheap Flights Starting at CA $419

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How Much Does it Cost To Fly To Dickinson County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Sep 18 - Fri, Sep 25
YYZ
Pearson Intl.
FSD
Sioux Falls Regional
CA $638 Roundtrip, found 2 days ago
CA $638
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Sep 18 from Pearson Intl. to Sioux Falls Regional, returning Fri, Sep 25, priced at CA $638 found 2 days ago
Tue, Mar 23 - Tue, Mar 30
YYZ
Pearson Intl.
FSD
Sioux Falls Regional
CA $679 Roundtrip, found 19 hours ago
CA $679
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Mar 23 from Pearson Intl. to Sioux Falls Regional, returning Tue, Mar 30, priced at CA $679 found 19 hours ago
Fri, Sep 18 - Fri, Sep 25
YYZ
Pearson Intl.
FSD
Sioux Falls Regional
CA $690 Roundtrip, found 2 days ago
CA $690
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Sep 18 from Pearson Intl. to Sioux Falls Regional, returning Fri, Sep 25, priced at CA $690 found 2 days ago
Tue, Mar 23 - Tue, Mar 30
YYZ
Pearson Intl.
FSD
Sioux Falls Regional
CA $700 Roundtrip, found 19 hours ago
CA $700
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Mar 23 from Pearson Intl. to Sioux Falls Regional, returning Tue, Mar 30, priced at CA $700 found 19 hours ago
Fri, Sep 18 - Fri, Sep 25
YYZ
Pearson Intl.
FSD
Sioux Falls Regional
CA $731 Roundtrip, found 2 days ago
CA $731
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Sep 18 from Pearson Intl. to Sioux Falls Regional, returning Fri, Sep 25, priced at CA $731 found 2 days ago
Tue, Mar 23 - Tue, Mar 30
YYZ
Pearson Intl.
FSD
Sioux Falls Regional
CA $762 Roundtrip, found 19 hours ago
CA $762
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Tue, Mar 23 from Pearson Intl. to Sioux Falls Regional, returning Tue, Mar 30, priced at CA $762 found 19 hours ago
Fri, Sep 18 - Fri, Sep 25
YYZ
Pearson Intl.
FSD
Sioux Falls Regional
CA $768 Roundtrip, found 2 days ago
CA $768
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Sep 18 from Pearson Intl. to Sioux Falls Regional, returning Fri, Sep 25, priced at CA $768 found 2 days ago
Fri, Sep 18 - Fri, Sep 25
YYZ
Pearson Intl.
FSD
Sioux Falls Regional
CA $779 Roundtrip, found 2 days ago
CA $779
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Sep 18 from Pearson Intl. to Sioux Falls Regional, returning Fri, Sep 25, priced at CA $779 found 2 days ago

Travelers ❤️ These Dickinson County 🏨

Lake Okoboji Resort & Conference Center

Lake Okoboji Resort & Conference Center

3 out of 5
1405 Highway 71 Okoboji IA
Book a stay at this golf hotel in Okoboji. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions West Okoboji Lake and Okoboji Summer Theatre are located nearby.
Opens in a new windowLake Okoboji Resort & Conference Center
AmericInn by Wyndham Okoboji

AmericInn by Wyndham Okoboji

3 out of 5
1005 Brooks Park Dr Okoboji IA
Book a stay at this golf hotel in Okoboji. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions West Okoboji Lake and Okoboji Summer Theatre are located nearby.
Opens in a new windowAmericInn by Wyndham Okoboji
Vintage Block Inn & Suites

Vintage Block Inn & Suites

2.5 out of 5
1107 Sanborn Ave Okoboji IA
Stay at this motel in Okoboji. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions West Okoboji Lake and Higgins Museum are located nearby.
9/10 Wonderful! (637 reviews)
"Great location. Friendly staff . Clean , updated rooms"

Reviewed on Aug 21, 2026

Opens in a new windowVintage Block Inn & Suites
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Bridges Bay Resort

Bridges Bay Resort

3.5 out of 5
630 Linden Drive Arnolds Park IA
Book a stay at this family-friendly resort in Arnolds Park. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions West Okoboji Lake and 'Boji Splash Indoor Waterpark Okoboji are located nearby.
7.6/10 Good! (708 reviews)
"We had a suite, which was nice. The door was dirty, the room was good but the bed wasn't super comfortable. The door to get to the little deck around, the seal was gone and didn't really close. The restaurants were good. Loved the bar. We had an amazing bartender, Aspen. She was the highlight of ..."

Reviewed on Aug 19, 2026

Opens in a new windowBridges Bay Resort
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 is the cheapest flight to Dickinson County?
Based on prices found over the last seven days, a roundtrip flight to Dickinson County started at as little as CA $638. If you can be flexible with your dates, it makes it easy to land a great bargain. This price was available on Travelocity for flights to Dickinson County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Dickinson County?
Work out your travel dates and then take off with any of the 15 airline companies that fly to Dickinson County. Consider booking with the popular air carrier, American Airlines. It operates around 290 flights a month to Milford, Dickinson County's major city, so finding your perfect fare should be a cinch.
What is the cheapest month to fly to Dickinson County?
Spend more of your money on epic experiences rather than airline tickets by hopping on a plane to Dickinson County in September. This is the best-priced month to jet off to this destination according to Travelocity's direct return flight demand from January to December last year. Scroll through our range of flights and get away on the cheap.
How can I check my flight status to Dickinson County?
There are a couple of useful ways to look up the status of your flight. You'll discover all the important information in our Trips portal, which is located at the top of our homepage. Sign in or create an account in seconds — you'll then be able to view and make changes to your bookings whenever you please. For those on the go, the Travelocity app can also help you look up the status of your flight to Dickinson County, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Dickinson County?
Snap up an incredible deal with Travelocity — our "Flexible dates" search option makes it so much easier. Enter the travel dates you want, then select the flexible dates box above your results to see the prices for surrounding days. CA $638 was the cheapest price for a roundtrip flight to Dickinson County in the last seven days on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Dickinson County with Travelocity?
Where to begin! With our cheap flights to Dickinson County, rental cars, hotels, activities and more, you'll find all you need for the perfect getaway with Travelocity. Reserve your cheap family flights and make use of our 24/7 customer assistance and free cancellations on most hotels if you need. Our goal is to offer stress-free travel when you book with us so that you can spend less time worrying and more time relaxing with your family and friends.
What are the most popular flight routes to Dickinson County?
With terrific connections, arranging flights to Dickinson County couldn't be easier. Here's a selection of the most popular flight routes to this must-see travel destination:

  • Chicago, IL (ORD-O'Hare Intl.) to Minneapolis - St. Paul Intl. Airport (MSP) - 3,198 flights a month.
  • Denver, CO (DEN-Denver Intl.) to Minneapolis - St. Paul Intl. Airport (MSP) - 2,223 flights a month.
  • Dallas, TX (DFW-Dallas-Fort Worth Intl.) to Minneapolis - St. Paul Intl. Airport (MSP) - 2,166 flights a month.

How much is a flight to Dickinson County on average?
Roundtrip flights to Dickinson County were priced between CA $638 and CA $779 in the last seven days. If you see a ticket price that best fits your budget, act fast. Cheap deals don't wait around for long! These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.