ORD - YQR

$178 Find Cheap Flights from Chicago to Regina - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Regina departing on 10/9. 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 Regina

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Regina, 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 Chicago to Regina, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$452
Typical prices: $303-$336
United Airlines
Sat 10/17Tue 10/20
ORD - YQR • 1 stop
Cheapest one-way
$178
WestJet
Fri 10/9
ORD - YQR • 1 stop
Top airlines
Cheapest • from $452 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Regina. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $505 (round-trip)
Shortest trip • 6h 28m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Regina!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Regina (ORD-YQR)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Regina 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 Chicago to Regina

Sat, Oct 17 - Tue, Oct 20
United Airlines Logo
6:00 am - 9:30 pm
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 am - 9:18 pm
YQR
-
ORD
10h 33m
1 stop
$452United Airlines
Thu, Sep 3 - Tue, Sep 8
Multiple Airlines Logo
5:55 am - 9:30 pm
ORD
-
YQR
16h 35m
1 stop
Multiple Airlines Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$459Multiple Airlines
Sat, Oct 17 - Tue, Oct 20
Air Canada Logo
8:45 am - 7:05 pm
ORD
-
YQR
11h 20m
2 stops
Air Canada Logo
12:40 pm - 7:48 pm
YQR
-
ORD
6h 08m
1 stop
$462Air Canada
Sat, Oct 17 - Tue, Oct 20
Air Canada Logo
8:45 am - 7:05 pm
ORD
-
YQR
11h 20m
2 stops
Air Canada Logo
5:45 am - 8:12 pm
YQR
-
ORD
13h 27m
2 stops
$470Air Canada
Sat, Oct 17 - Tue, Oct 20
Air Canada Logo
8:45 am - 7:05 pm
ORD
-
YQR
11h 20m
2 stops
Air Canada Logo
5:45 am - 8:12 pm
YQR
-
ORD
13h 27m
2 stops
$471Air Canada
Thu, Jul 16 - Thu, Jul 23
United Airlines Logo
6:00 am - 9:30 pm
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 am - 12:44 am
YQR
-
ORD
13h 59m
1 stop
$476United Airlines
Thu, Nov 19 - Mon, Nov 23
Air Canada Logo
8:35 pm - 10:43 am
ORD
-
YQR
14h 08m
1 stop
Air Canada Logo
5:00 am - 1:13 pm
YQR
-
ORD
8h 13m
1 stop
$477Air Canada
Thu, Nov 19 - Mon, Nov 23
Air Canada Logo
10:15 am - 11:27 pm
ORD
-
YQR
13h 12m
1 stop
Air Canada Logo
5:00 am - 2:52 pm
YQR
-
ORD
9h 52m
2 stops
$486Air Canada
Thu, Aug 13 - Fri, Aug 21
Delta Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
Delta Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$530Delta
Thu, Nov 19 - Mon, Nov 23
Delta Logo
5:30 am - 7:21 pm
ORD
-
YQR
13h 51m
2 stops
Delta Logo
12:45 pm - 11:50 pm
YQR
-
ORD
11h 05m
2 stops
$536Delta
Booking Insights

KAYAK's insights & trends for Chicago to Regina flights

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

How much is a round-trip flight from Chicago O'Hare Intl Airport to Regina?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Regina departing in October.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Regina, 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 Chicago O'Hare Intl Airport to Regina is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $1,145 and $863 respectively.

Good to know

Low seasonOctober
Cheapest flight$178
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Chicago to Regina

When to book flights from Chicago to Regina

Are your dates flexible? Find out the best times to travel from Chicago to Regina 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 Chicago to Regina flights

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

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Regina was $178 for a one-way ticket and $452 for a round-trip.

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

    A passport is required to fly from Chicago to Regina.

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

    On your way to Regina, you’ll fly out from Chicago O'Hare Intl. You’ll be landing at Regina.

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

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

  • Which airline alliances offer flights from Chicago to Regina?

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

  • Which is the best airline for flights from Chicago to Regina, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Regina are Delta and United Airlines. With an average price for the route of $609 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $709 and an overall rating of 7.4.

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

    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 Chicago to Regina.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Regina from Chicago 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 Chicago to Regina?

    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 Regina with an airline and back to Chicago with another airline. Booking your flights between Chicago and YQR 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 Chicago to Regina?

    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 Regina from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Regina

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Regina. 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 Chicago to Regina? 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.
7.8
DeltaOverall score based on 8449 reviews
7.2Food
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
Airline reviews

Very easy to use and convenient, you can perform any action within the same portal

10.0 ExcellentMurat, Apr 2026
ORD - LGA
Read more Delta reviews

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

Delta airlines charge $ 30,oo US DOLLARS for the check in for a suitcase in the baggage hold

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

Not United Airlines' fault. It's ORL airport's fault.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Delay and keep changing gates. I have to run around from B to C then to E.

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

Flight was delayed due to weather and clogged toilet. Had to deplane. Flight was 3 hours delayed. Crew was awesome and offered water and snacks.

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

Information on your arrival and departure airports