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YQR - ORD

Find cheap flights from Regina to Chicago from $171

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 5/23. 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
Fri 5/24
Fri 5/31

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 45,119,101 times on KAYAK, and here is why:

Save 22% 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.

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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
8:15 am - 7:10 pmYQR-ORD
9h 55m1 stop
7:00 am - 2:28 pmORD-YQR
8h 28m1 stop
Mon, Jul 8 - Thu, Jul 18
8:15 am - 5:19 pmYQR-ORD
8h 04m1 stop
8:05 pm - 2:28 pmORD-YQR
19h 23m1 stop
Wed, Jul 17 - Thu, Jul 25
8:15 am - 5:18 pmYQR-ORD
8h 03m1 stop
8:05 pm - 2:28 pmORD-YQR
19h 23m1 stop
Mon, Jun 3 - Fri, Jun 14
7:35 pm - 9:54 amYQR-ORD
13h 19m1 stop
11:00 am - 6:40 pmORD-YQR
8h 40m1 stop
$351Air Canada
Find Deal
Sun, Jun 23 - Tue, Jun 25
7:20 am - 5:05 pmYQR-ORD
8h 45m1 stop
6:00 am - 2:28 pmORD-YQR
9h 28m1 stop
$355Delta
Find Deal
Mon, Jun 3 - Sat, Jun 15
8:15 am - 4:49 pmYQR-ORD
7h 34m1 stop
6:00 am - 2:28 pmORD-YQR
9h 28m1 stop
$361Delta
Find Deal
Wed, Jun 5 - Sat, Jun 15
10:25 am - 10:02 pmYQR-ORD
10h 37m1 stop
1:00 pm - 6:40 pmORD-YQR
6h 40m1 stop
$371Air Canada
Find Deal
Tue, Jun 18 - Tue, Jun 25
7:15 am - 4:57 pmYQR-ORD
8h 42m1 stop
5:55 pm - 9:58 amORD-YQR
17h 03m2 stops
$418WestJet
Find Deal
Thu, Jul 11 - Tue, Jul 16
7:15 am - 4:57 pmYQR-ORD
8h 42m1 stop
5:55 pm - 12:57 amORD-YQR
8h 02m1 stop
$420WestJet
Find Deal
Thu, Jul 11 - Mon, Jul 15
6:00 pm - 7:57 amYQR-ORD
12h 57m1 stop
11:00 am - 6:40 pmORD-YQR
8h 40m1 stop
$425United Airlines
Find Deal
Thu, Jul 18 - Sat, Jul 27

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 Monday, 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 $381 on average. On the other hand, the most expensive months are April and February, where the average cost of tickets is $1,677 and $1,028 respectively.

Good to know

Low season

September

High season

May

Cheapest flight

$171
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 12% 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 $171 for a one-way ticket and $280 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?

    Star Alliance, and SkyTeam are the airline alliances operating flights between Regina and Chicago, with Star Alliance 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 6857 reviews
7.2boarding
7.8crew
7.0comfort
6.8entertainment
6.2food
Airline reviews

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

10.0 ExcellentJoshua, Apr 2024YYZ - DEN
Read more about Air Canada reviews

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

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

I didn’t like the fact that all the customs officers went to lunch so I was in line for 90 minutes due to where the staff directed me. We were told three very different reasons for why the plane was delayed. It was a crowded plane with difficult storage situations for the Carry On bags. The Air Canada airline staff were all very good and professional. I was so disappointed in my cheese and fruit box as the cheese had molded and the fruit wasn’t fresh so I couldn’t eat the majority of the food. This was the last meal I could find as the restaurants had closed when I got in to my destination. I think you could work on improving the food quality.

There was no entertainment at our seats. The flight was comfortable and we had leg room. The snack we had was really good.

Economy seats were surprisingly comfortable, and snacks not too bad. Checked luggage arrived at destination without problems. It was annoying to wait until last to board as lowest-tier seats but understand it’s difficult to gauge when loading a full plane At least checked carryon luggage seemed to come off first. Annoying to have to use app to order food/drink when wifi availability didn’t allow time for it. Advance communication would have helped Food on menu seemed highly processed and unpalatable, overpriced and over packaged. So maybe a good thing to have missed chance to order

Once again my complaint is how close the seats are together. Also, the bathrooms were not very clean by the second half of the flight.

Excellent in flight service, perhaps the best we've ever had. Business class feels tired and needs improvement to compete with other airlines. The food looked good but tasted terrible. Check in was quick, the flight arrived early and our luggage was on our flight with us.

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.
5/23Thu
1 stop
9h 48mYQR-ORD
$171
5/23Thu
2 stopsAir Canada
13h 26mYQR-ORD
$212
5/23Thu
3 stops
16h 20mYQR-ORD
$311

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Last minute flights from Regina to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Regina to Chicago that are departing in the next 10 days.
4/29Mon
multi-stopDelta
9h 20mYQR-ORD
5/1Wed
multi-stopDelta
9h 08mORD-YQR
$584
4/29Mon
multi-stopDelta
12h 06mYQR-ORD
5/1Wed
multi-stopDelta
9h 08mORD-YQR
$652
4/29Mon
multi-stopWestJet
9h 20mYQR-ORD
5/1Wed
multi-stopWestJet
10h 06mORD-YQR
$797
4/29Mon
multi-stopWestJet
9h 20mYQR-ORD
5/1Wed
multi-stopWestJet
19h 36mORD-YQR
$871

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Regina - Chicago Flights

Departure:

Regina (YQR)Canada

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Regina

Cabin classes: