YQR - ORD

C$ 163 Find Cheap Flights from Regina to Chicago

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 11/5. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
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
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Everything you should know

Cheapest round-trip
C$ 244
WestJet
Fri 10/4Fri 17/4
YQR - ORD • 1 stop
Cheapest one-way flights
C$ 163
WestJet
Mon 11/5
YQR - ORD • 1 stop
Top airlines
WestJet
Cheapest • from C$ 244 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Not available
There are currently no direct flights between Regina and Chicago. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Denver (DEN)
Cheapest • Avg C$ 384 (round-trip)
Minneapolis (MSP)
Shortest trip • 5h 51m (one-way)
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Regina to Chicago

Fri, 10 Apr - Fri, 17 Apr
WestJet Logo
5:10 a.m. - 1:35 p.m.
YQR
-
ORD
7h 25m
1 stop
WestJet Logo
2:20 p.m. - 8:06 p.m.
ORD
-
YQR
6h 46m
1 stop
C$ 244WestJet
Sat, 25 Apr - Thu, 14 May
WestJet Logo
3:25 p.m. - 4:40 p.m.
YQR
-
ORD
24h 15m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 367WestJet
Fri, 10 Apr - Fri, 17 Apr
WestJet Logo
5:10 a.m. - 1:35 p.m.
YQR
-
ORD
7h 25m
1 stop
WestJet Logo
2:20 p.m. - 9:30 a.m.
ORD
-
YQR
44h 10m
2 stops
C$ 400WestJet
Mon, 30 Mar - Thu, 2 Apr
United Airlines Logo
5:00 a.m. - 2:00 p.m.
YQR
-
ORD
8h 00m
1 stop
United Airlines Logo
2:05 p.m. - 9:30 p.m.
ORD
-
YQR
8h 25m
1 stop
C$ 426United Airlines
Fri, 5 Jun - Sun, 7 Jun
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 433WestJet
Sat, 25 Apr - Thu, 14 May
WestJet Logo
3:25 p.m. - 4:40 p.m.
YQR
-
ORD
24h 15m
1 stop
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 456WestJet
Fri, 5 Jun - Sun, 7 Jun
WestJet Logo
11:50 a.m. - 4:40 p.m.
YQR
-
ORD
27h 50m
2 stops
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 469WestJet
Tue, 10 Mar - Fri, 13 Mar
Multiple Airlines Logo
5:10 a.m. - 6:08 a.m.
YQR
-
ORD
23h 58m
2 stops
Multiple Airlines Logo
6:40 p.m. - 6:31 p.m.
ORD
-
YQR
24h 51m
1 stop
C$ 522Multiple Airlines
Mon, 30 Mar - Thu, 2 Apr
Multiple Airlines Logo
6:00 a.m. - 2:30 p.m.
YQR
-
ORD
31h 30m
2 stops
Multiple Airlines Logo
6:25 p.m. - 6:21 p.m.
ORD
-
YQR
24h 56m
1 stop
C$ 528Multiple Airlines
Fri, 5 Jun - Sun, 7 Jun
WestJet Logo
11:50 a.m. - 4:40 p.m.
YQR
-
ORD
27h 50m
2 stops
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 595WestJet
Booking Insights

KAYAK's insights & trends for Regina to Chicago flights

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.

Which airlines provide the cheapest flights from Regina to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Regina to Chicago were found on WestJet (C$ 244) and United Airlines (C$ 426).

Good to know

Cheapest flightC$ 163
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 C$ 163 for a one-way ticket and C$ 244 for a round-trip.

  • Which airports will I be using when flying from Regina to Chicago?

    Regina and Chicago are both served by 1 main airport. You will leave Regina from Regina and will be arriving at Chicago O'Hare Intl.

  • 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 is the only airline alliance operating flights between Regina and Chicago.

  • 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 travellers 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.

  • 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.

Reviews of the 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.
7.4
United AirlinesOverall score based on 9345 reviews
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

10.0 ExcellentDr. Joseph, Feb 2026
DCA - ORD
Read more United Airlines reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Everything you need to know for your flight from Regina to Chicago

Information on your arrival and departure airports