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Cheap flights from Regina to Chicago from C$ 229

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 13/9. Fares are subject to change and may not be available on all flights or dates of travel.
YQR — CHI
4 Aug — 11 Aug1
1 adult

Cheap flight deals from Regina to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Regina (YQR) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 30 July 2025.

Round-trip from

C$ 410

One-way from

C$ 229

Popular in

November

Cheapest in

May

Average price

C$ 650
Air Canada
  • Air Canada
  • 20/11-25/11
  • 2 total stops
  • 15h 25m total
  • Regina to Chicago
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13/9
  • 13/9
  • 1 total stop
  • 9h 30m total
  • Regina to Chicago
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Highest demand for flights based on searches. 17% potential increase in price (C$ 187 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 35 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Regina to Chicago

Cheapest flights from Regina to Chicago
Explore the most affordable flight options available from Regina to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 July 2025.

Thu 20/115:00 a.m.YQR - ORD
1 stop8h 01mAir Canada
Tue 25/113:55 p.m.ORD - YQR
1 stop7h 24mAir Canada
Deal found 29/7C$ 410
Tue 5/810:15 a.m.YQR - ORD
1 stop24h 47mMultiple Airlines
Thu 14/811:21 a.m.ORD - YQR
2 stops25h 06mMultiple Airlines
Deal found 29/7C$ 855
Tue 5/810:15 a.m.YQR - ORD
1 stop24h 47mWestJet
Thu 14/85:30 p.m.ORD - YQR
1 stop6h 32mWestJet
Deal found 29/7C$ 927
Wed 24/1211:45 a.m.YQR - MDW
1 stop5h 52mDelta
Sun 28/1211:48 a.m.MDW - YQR
1 stop6h 29mDelta
Deal found 29/7C$ 928
Tue 5/810:15 a.m.YQR - MDW
1 stop6h 24mWestJet
Thu 14/812:43 p.m.MDW - YQR
2 stops11h 19mWestJet
Deal found 29/7C$ 939

Cheapflights Fare Finder

 
Customize your flight search to find flights from Regina to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 30 July 2025.
Use the filters below to find and compare flights from Regina to Chicago that are best for you.

Fly from

Regina

Fly to

Chicago

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 20/11

5:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Tue 25/11

3:55 p.m.-11:19 p.m.

1 stop7h 24m

C$ 410

ReginaChicago

YQR - MDW

YQRMDW

Regina

Wed 24/12

11:45 a.m.-5:37 p.m.

1 stop5h 52m

Chicago Midway

Sun 28/12

11:48 a.m.-6:17 p.m.

1 stop6h 29m

C$ 928

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 20/11

11:45 a.m.-1:09 p.m.

1 stop25h 24m

Chicago Midway

Tue 25/11

10:35 a.m.-3:53 p.m.

2 stops29h 18m

C$ 939

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 13/9

5:30 p.m.-4:43 p.m.

2 stops22h 13m

C$ 229

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 13/9

6:55 a.m.-7:12 p.m.

3 stops35h 17m

C$ 330

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 13/9

6:00 a.m.-11:17 p.m.

3 stops16h 17m

C$ 475

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 13/9

10:15 a.m.-5:35 p.m.

1 stop6h 20m

C$ 828

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/7

Best time to book a flight from Regina to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Regina with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Regina to Chicago?

Currently, January is the cheapest month in which you can book a flight from Regina to Chicago (average of C$ 261). Flying from Regina to Chicago in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YQR to CHI?

Find hourly flight availability from Regina to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 30 July 2025.

One of the essential ways to save on airfare from Regina to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 34% on airfare.

What’s the top layover airport for flights from Regina to Chicago?

Share of one-stop round-trip flights from Regina to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 50% of one-stop itineraries from Regina to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Regina to Chicago?

Average round-trip fare for 1-stop flights from Regina to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 326.

What’s the fastest layover option from Regina to Chicago?

Shortest average travel time for 1-stop one-way flights from Regina to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 5h 47m.

Which airport typically offers the quickest layover for flights from Regina to Chicago?

Average layover duration for 1-stop one-way flights from Regina to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 50m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 30 July 2025.
Read through reviews of airlines operating flights from Regina to Chicago, such as Delta,WestJet, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews
Check prices

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,975 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Canada
7.1
Good
9,837 reviews
Delta
8.0
Very good
7,980 reviews
Check prices

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

Related info for your journey

Find useful and relevant information for your journey from Regina to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Regina to Chicago?

    Regina (YQR) is the airport you will fly out of if you book a flight from Regina to Chicago. You should not have trouble finding flights to Chicago from Regina; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the Regina airport to Chicago. It is only a 4.0 km journey to Regina (YQR) from Regina’s city centre.

  • What are the cheapest airlines flying from Regina to Chicago round-trip?

    Air Canada, at C$ 410, was found to be the cheapest airline from Regina to Chicago.Alternate airlines to your destination round-trip include Delta and WestJet. Air Canada is 34% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Regina to Chicago that include hotel bookings?

    Yes. In addition to deals on Regina to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Regina to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Regina to Chicago.

  • Can I find deals for business class flights from Regina to Chicago?

    Yes. Cheapflights offers flight deals from Regina to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Regina to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Regina to Chicago (average of C$ 261). Flying from Regina to Chicago in March is currently the most expensive (average of C$ 352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Regina to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Saskatoon to O'Hare Intl flights
Saskatoon to Midway flights
Regina to O'Hare Intl flights
Saskatoon to St. Louis flights

Top 3 airlines flying from Regina to Chicago

Discover the top 3 airlines that operate flights from Regina to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 30 July 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 396AverageC$ 805FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 402AverageC$ 757FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 463AverageC$ 587FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Regina to Chicago?

Deals for Regina to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Regina to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Regina to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Regina to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Regina shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Regina to Chicago become cheaper?

Of course! You can now track prices for flights from Regina to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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