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Find cheap flights from Regina to Chicago from $178

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Regina to Chicago departing on 6/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 6/12
Wed 6/19

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Regina to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Regina to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 41,771,603 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Regina to Chicago (YQR-ORD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Regina to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:00 pm - 5:05 pmYQR-ORD
23h 05m1 stop
5:55 pm - 12:57 amORD-YQR
8h 02m1 stop
$308WestJet
Find Deal
Sun, Jun 9 - Sun, Jun 16
8:15 am - 7:30 pmYQR-ORD
10h 15m1 stop
6:25 am - 12:57 amORD-YQR
19h 32m3 stops
$327
Find Deal
Sun, Jun 9 - Sun, Jun 16
8:15 am - 11:58 pmYQR-ORD
14h 43m2 stops
6:07 am - 2:28 pmORD-YQR
9h 21m1 stop
$340Delta
Find Deal
Sat, May 25 - Wed, May 29
8:15 am - 2:42 pmYQR-ORD
5h 27m1 stop
9:36 am - 2:28 pmORD-YQR
5h 52m1 stop
$347Delta
Find Deal
Sat, May 25 - Wed, May 29
8:35 pm - 7:06 pmYQR-ORD
21h 31m3 stops
6:25 am - 12:57 amORD-YQR
19h 32m3 stops
$364
Find Deal
Sun, Jun 9 - Sun, Jun 16
8:15 am - 9:14 amYQR-ORD
23h 59m2 stops
6:25 am - 12:57 amORD-YQR
19h 32m3 stops
$386
Find Deal
Sun, Jun 9 - Sun, Jun 16
8:15 am - 9:14 amYQR-ORD
23h 59m2 stops
5:55 pm - 12:57 amORD-YQR
8h 02m1 stop
$393
Find Deal
Sun, Jun 9 - Sun, Jun 16
7:35 pm - 9:54 amYQR-ORD
13h 19m1 stop
9:15 pm - 9:30 amORD-YQR
13h 15m1 stop
$521Air Canada
Find Deal
Fri, Jun 21 - Sun, Jun 30
7:15 am - 4:57 pmYQR-ORD
8h 42m1 stop
5:55 pm - 9:58 amORD-YQR
17h 03m2 stops
$644WestJet
Find Deal
Fri, Jun 21 - Sun, Jun 30
3:05 pm - 4:40 amYQR-ORD
12h 35m2 stops
6:00 am - 9:31 pmORD-YQR
16h 31m2 stops
$790
Find Deal
Fri, Jun 21 - Sun, Jun 30

Flights from Regina to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Regina to Chicago to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Regina to Chicago?

The average price of all flights from Regina to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago on a Monday and more expensive on a Thursday. On your return trip to Regina, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

What is the cheapest month to fly from Regina to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Regina to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Regina to Chicago O'Hare Intl Airport is January, where tickets cost $210 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is $799 and $702 respectively.

Which airlines provide the cheapest flights from Regina to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Regina to Chicago found on KAYAK was with WestJet for $178. WestJet proposed a round-trip connection from $308 and Delta from $340.

Good to know

Low season

September

High season

February

Cheapest flight

$178
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 36% lower on average.
Flight from Regina to Chicago

When to book flights from Regina to Chicago

Are your dates flexible? Find out the best times to travel from Regina to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Regina to Chicago flights

  • What is the cheapest flight from Regina to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Regina to Chicago O'Hare Intl Airport was $178 for a one-way ticket and $308 for a round-trip.

  • Do I need a passport to fly between Regina and Chicago?

    Yes, you’ll need a passport to travel to Chicago from Regina.

  • Which aircraft models fly most regularly from Regina to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Regina to Chicago?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Regina and Chicago, with SkyTeam being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Regina to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Regina to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Regina to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Regina is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Regina to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Regina with another airline. Booking your flights between Regina and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Regina to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Regina up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Regina to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Regina to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Regina to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.0
Air CanadaOverall score based on 6937 reviews
7.0Comfort
7.8Crew
6.8Entertainment
6.2Food
7.2Boarding
Airline reviews

Pretty good service and US Migratory officers providing services in Canada was awesome, because the arrival was quick and smooth

10.0 ExcellentAnonymous, May 2024YUL - JFK
Read more about Air Canada reviews

Pretty good service and US Migratory officers providing services in Canada was awesome, because the arrival was quick and smooth

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

Rouge needs to offer seats with better pitch in economy. Many sick people on a full flight.

Overall, I would have to say my experience with Air Canada was mediocre their DC tens. Need to be updated not comfortable at all. Only one out of my four flights was decent. The staffing was very nice. Going through customs in Montreal was quick and easy. Air Canada has room for improvement with their facilities.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

The experience was generally above average. The only downside was the absence of WiFi during my flight from Vancouver to San Francisco.

on demand entertainment in seat back awesome Check in Kiosk too demanding with endless demand for more information information then says go to counter. Counter agent unfriendly. Do it yourself check in luggage procedure not intuitive, upset employees frustrated the whole procedure.

It was an excellent experience, traveling from Toronto to Denver with United.

Book cheap flights from Regina to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Regina to Chicago found on KAYAK in the last 72 hours.
6/7Fri
1 stopWestJet
19h 30mYQR-ORD
$178
6/7Fri
2 stopsDelta
9h 48mYQR-ORD
$299

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Regina - Chicago Flights

Departure:

Regina (undefined)Canada

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Regina

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