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YQR - ORD

$246 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 6/29. 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 7/10
Wed 7/17

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 42,898,604 times on KAYAK, and here is why:

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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
7:35 pm - 10:01 amYQR-ORD
13h 26m2 stops
12:00 pm - 6:40 pmORD-YQR
7h 40m1 stop
$314Air Canada
Find Deal
Tue, Jul 9 - Tue, Jul 16
7:35 pm - 7:57 amYQR-ORD
11h 22m1 stop
9:15 pm - 9:30 amORD-YQR
13h 15m1 stop
$350Air Canada
Find Deal
Tue, Jul 16 - Sat, Jul 20
3:20 pm - 7:52 amYQR-ORD
15h 32m2 stops
9:15 pm - 9:30 amORD-YQR
13h 15m1 stop
$355Air Canada
Find Deal
Tue, Jul 16 - Sat, Jul 20
8:35 pm - 6:36 pmYQR-ORD
21h 01m3 stops
5:35 pm - 9:58 amORD-YQR
17h 23m2 stops
Sat, Jun 29 - Tue, Jul 2
8:15 am - 8:44 amYQR-ORD
23h 29m1 stop
9:39 am - 2:28 pmORD-YQR
5h 49m1 stop
$408Delta
Find Deal
Wed, Jul 31 - Fri, Aug 2
8:35 pm - 6:36 pmYQR-ORD
21h 01m3 stops
5:35 pm - 10:52 amORD-YQR
18h 17m3 stops
Sat, Jun 29 - Tue, Jul 2
8:15 am - 5:46 pmYQR-ORD
32h 31m3 stops
9:33 pm - 11:12 pmORD-YQR
26h 39m3 stops
Tue, Jul 16 - Sat, Jul 20
6:15 am - 4:57 pmYQR-ORD
9h 42m1 stop
7:01 am - 12:57 amORD-YQR
18h 56m3 stops
Wed, Jul 31 - Fri, Aug 2
8:15 am - 9:03 pmYQR-ORD
11h 48m2 stops
9:20 am - 2:28 pmORD-YQR
6h 08m1 stop
$528Delta
Find Deal
Sat, Jun 29 - Wed, Jul 3
8:15 am - 9:57 pmYQR-ORD
12h 42m1 stop
9:15 am - 11:17 pmORD-YQR
15h 02m2 stops
$579WestJet
Find Deal
Sat, Jun 29 - Tue, Jul 2

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.

Good to know

Low season

September

High season

February

Cheapest flight

$246
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 35% 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 $246 for a one-way ticket and $314 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 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 7070 reviews
7.2Boarding
7.0Comfort
7.8Crew
6.8Entertainment
6.2Food
Airline reviews

Experienced flight cancelations and delays in 5 days. They seem pretty common to AC. Experienced with one of AC's check-in agents at the counter of a big liar. She lied and acted (yes like acting in a movie) that an early flight was fully booked and refused to rebook me, but my flight was delayed two hours so I could not make my connection. Later, I got help at the gate to switch the early flight (Big thanks to that agent). Ater boading, I found the early flight was only 2/3 full meaning there was almost one vacant seat in a 3-person seater, and multiple empty 3-seaters. AC is wired that it is filled with good and bad employees. BTW, AC employees seem never smile, or they don't know how.

2.0 MediocreJ, Jun 2024YYZ - SFO
Read more about Air Canada reviews

Experienced flight cancelations and delays in 5 days. They seem pretty common to AC. Experienced with one of AC's check-in agents at the counter of a big liar. She lied and acted (yes like acting in a movie) that an early flight was fully booked and refused to rebook me, but my flight was delayed two hours so I could not make my connection. Later, I got help at the gate to switch the early flight (Big thanks to that agent). Ater boading, I found the early flight was only 2/3 full meaning there was almost one vacant seat in a 3-person seater, and multiple empty 3-seaters. AC is wired that it is filled with good and bad employees. BTW, AC employees seem never smile, or they don't know how.

Not much food/snacks. I had just tea and it was so bitter.

My husbands flight last night Vancouver/Sydney was 90 minutes late in leaving. My flight tonight Vancouver/Seattle was also late in departing.

My mother, 80years old, had arranged for wheelchair assist to and from the aircraft cabin and in the airport but, no one showed up for her to de-plane. Apart from Air Canada having a reputation of being late for every leg of its flight so nothing was new this time so this time they did worse by not assisting seniors. I guess our whole family is done with this airline

Flights delayed over 4 hours with no compensation. No agents at counters to assist with re-booking.

Seating for almost 3 hours in the plan before aircraft takeoff. Very exhausted .

The bathroom did not have hand soap. That is unacceptable.

The only problem I encountered was they changed the gate on me while I was sitting down but no one notified me, they had sent me an email and by coincidence I checked it and found out that they had changed my boarding terminal. No one notified me and when I had asked the lady she told me yes this is the spot while they had already changed to another gate/terminal

I was seated next to someone who was, to be polite, not a small person. I had to press myself against the wall as I had no personal space. Aside from that the crew was wonderful and they got me home safely, which is the most important part of my journey. I am very appreciative to your air crews for the job they have, which isn't easy, and appreciative of the fact that they are professional and courteous. The employees I encountered on my journey, with the few exceptions I mentioned in a previous review, are a credit to Air Canada.

Air Canada had a lot of delays on our flight going back to Seattle. So much inconvenience for a long trip.

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.
6/29Sat
2 stops
22h 45mYQR-ORD
$246
6/29Sat
3 stops
34h 21mYQR-ORD
$272
6/29Sat
1 stopWestJet
12h 42mYQR-ORD
$303

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Regina - Chicago Flights

Departure:

Regina (YQR)Canada

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Regina

Cabin classes: