Flights from Stillwater to Chicago Starting at £156

We've found these cheap flights for you. You can book one-way or return flight tickets.

Round-trip
One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

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Cheapest flights

From price

9 16
16 23
23 30
Apr

30 6
6 13
13 20
20 27
May

27 4
4 11
11 18
18 25
Jun

25 1

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

FAQ

When are flight tickets from Stillwater (SWO) to Chicago (CHI) the cheapest?

Airlines adjust prices for flights from Stillwater to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Stillwater (SWO) to Chicago (CHI) cost?

According to Trip.com's data, the lowest price is around £421.
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
How many airports in Chicago (CHI)?

There are 3 airport(s) in Chicago (CHI): Midway International Airport, O'Hare International Airport and Chicago Rockford International Airport.

How to find a cheap flight from Stillwater to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Stillwater to Chicago. Book your flights at the right time and save more.

Be flexible with your travel dates to get the cheapest flight from Stillwater to Chicago.

Simply tap "Date" on the flight search bar to browse through the calendar and check out airfare from Stillwater to Chicago over the next 6 months in 2025. If you're planning to fly within the next three months, it looks like the most affordable option is on Sat, May 3, with one-way flights priced at just £156.

Compare cheap flight deals from Stillwater to Chicago across hundreds of airlines.

With our extensive search, you can compare prices from over 500 airlines to find the cheapest flight tickets from Stillwater to Chicago. The cheapest airline for this route is American Airlines.

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Book early or wait until the last minute.

It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.

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For the best travel flight booking experience, download the Trip.com app. You can search for cheap flights from Stillwater to Chicago and snag some exclusive deals just for you.

Flight Information from Stillwater to Chicago

Cheapest direct flight price	£156
Off-season travel month	May
Peak season for travel	December
Flight distance	1,033.4km
Popular airline	American Airlines