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Cheap flights from Regina to Chicago from C$ 222

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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
YQR — CHI
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 356

One-way from

C$ 222

Popular in

November

Cheapest in

October

Average price

C$ 589
WestJet
  • WestJet
  • 6/11-14/11
  • 2 total stops
  • 48h 20m total
  • Regina to Chicago
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11/1
  • 11/1
  • 1 total stop
  • 28h 05m total
  • Regina to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 87 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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 11 September 2025.

Thu 6/1110:40 a.m.YQR - ORD
1 stop26h 55mWestJet
Fri 14/112:20 p.m.ORD - YQR
1 stop21h 25mWestJet
Deal found 10/9C$ 356
Thu 6/1111:45 a.m.YQR - ORD
2 stops36h 30mMultiple Airlines
Fri 14/112:20 p.m.ORD - YQR
1 stop21h 25mMultiple Airlines
Deal found 10/9C$ 391
Wed 5/1112:15 p.m.YQR - ORD
2 stops18h 10mMultiple Airlines
Fri 14/112:20 p.m.ORD - YQR
1 stop21h 25mMultiple Airlines
Deal found 10/9C$ 468
Wed 5/1110:45 a.m.YQR - ORD
1 stop8h 55mUnited Airlines
Thu 13/112:40 p.m.ORD - YQR
1 stop8h 11mUnited Airlines
Deal found 10/9C$ 470
Wed 8/109:45 a.m.YQR - ORD
1 stop13h 14mUnited Airlines
Wed 15/107:10 a.m.ORD - YQR
1 stop15h 26mUnited Airlines
Deal found 10/9C$ 477
Wed 5/1110:45 a.m.YQR - ORD
1 stop8h 55mUnited Airlines
Thu 6/112:40 p.m.ORD - YQR
1 stop8h 11mUnited Airlines
Deal found 10/9C$ 491
Wed 5/1110:45 a.m.YQR - ORD
1 stop8h 55mUnited Airlines
Fri 14/118:15 p.m.ORD - YQR
1 stop14h 24mUnited Airlines
Deal found 10/9C$ 492
Thu 6/114:15 p.m.YQR - ORD
1 stop29h 28mMultiple Airlines
Thu 13/116:30 p.m.ORD - YQR
2 stops23h 47mMultiple Airlines
Deal found 10/9C$ 524
Thu 6/114:15 p.m.YQR - ORD
1 stop29h 28mMultiple Airlines
Sat 15/115:45 p.m.ORD - YQR
2 stops24h 32mMultiple Airlines
Deal found 10/9C$ 538
Thu 6/1110:45 a.m.YQR - ORD
2 stops24h 51mUnited Airlines
Thu 13/118:50 a.m.ORD - YQR
2 stops14h 01mUnited Airlines
Deal found 10/9C$ 557
Thu 6/1111:45 a.m.YQR - MDW
2 stops34h 23mMultiple Airlines
Sat 15/112:57 p.m.MDW - YQR
1 stop25h 18mMultiple Airlines
Deal found 10/9C$ 710
Thu 6/1111:45 a.m.YQR - MDW
1 stop5h 58mDelta
Thu 13/119:32 a.m.MDW - YQR
2 stops8h 45mDelta
Deal found 10/9C$ 711

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 11 September 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 6/11

10:40 a.m.-1:35 p.m.

1 stop26h 55m

Chicago O'Hare Intl

Fri 14/11

2:20 p.m.-11:45 a.m.

1 stop21h 25m

C$ 356

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 6/11

11:45 a.m.-12:15 a.m.

2 stops36h 30m

Chicago O'Hare Intl

Fri 14/11

2:20 p.m.-11:45 a.m.

1 stop21h 25m

C$ 391

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 5/11

12:15 p.m.-6:25 a.m.

2 stops18h 10m

Chicago O'Hare Intl

Fri 14/11

2:20 p.m.-11:45 a.m.

1 stop21h 25m

C$ 468

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 5/11

10:45 a.m.-7:40 p.m.

1 stop8h 55m

Chicago O'Hare Intl

Thu 13/11

2:40 p.m.-10:51 p.m.

1 stop8h 11m

C$ 470

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 8/10

9:45 a.m.-11:59 p.m.

1 stop13h 14m

Chicago O'Hare Intl

Wed 15/10

7:10 a.m.-9:36 p.m.

1 stop15h 26m

C$ 477

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 5/11

10:45 a.m.-7:40 p.m.

1 stop8h 55m

Chicago O'Hare Intl

Thu 6/11

2:40 p.m.-10:51 p.m.

1 stop8h 11m

C$ 491

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 5/11

10:45 a.m.-7:40 p.m.

1 stop8h 55m

Chicago O'Hare Intl

Fri 14/11

8:15 p.m.-10:39 a.m.

1 stop14h 24m

C$ 492

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 7/11

10:45 a.m.-10:50 p.m.

1 stop12h 05m

Chicago O'Hare Intl

Fri 14/11

8:15 p.m.-10:39 a.m.

1 stop14h 24m

C$ 492

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 6/11

4:15 p.m.-9:43 p.m.

1 stop29h 28m

Chicago O'Hare Intl

Sat 15/11

5:45 p.m.-6:17 p.m.

2 stops24h 32m

C$ 538

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 6/11

10:45 a.m.-11:36 a.m.

2 stops24h 51m

Chicago O'Hare Intl

Thu 13/11

8:15 p.m.-10:39 a.m.

1 stop14h 24m

C$ 554

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 25 results
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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$ 349). 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 11 September 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.

How much does it cost to fly round-trip from Regina to Chicago?

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 52% 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$ 327.

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 44m.

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 Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 1h 41m.

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 11 September 2025.
Read through reviews of airlines operating flights from Regina to Chicago, such as WestJet and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,091 reviews
Check prices

Entertainment

6.1

Food

6.2

Boarding

7.4

Comfort

7.1

Overall

7.2

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
WestJet
7.2
Good
3,091 reviews
WestJet
7.2
Good
3,091 reviews
Check prices

Entertainment

6.1

Food

6.2

Boarding

7.4

Comfort

7.1

Overall

7.2

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
Air Canada
7.1
Good
10,000 reviews
WestJet
7.2
Good
3,091 reviews
Check prices

Entertainment

6.1

Food

6.2

Boarding

7.4

Comfort

7.1

Overall

7.2

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.

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.

  • How long is the flight from Regina to Chicago?

    WestJet, United Airlines, and Delta can get you from Regina to Chicago in just under 5h 58m. Your travel time can differ by up to 20h 57m. There are 1613 km between Regina and Chicago. Both multi-stop and direct flights can be found to your destination and back.

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

    WestJet, at C$ 375, was found to be the cheapest airline from Regina to Chicago.Alternate airlines to your destination round-trip include Air Canada and Delta. WestJet is 40% 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$ 349). 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
Regina to O'Hare Intl flights
Saskatoon to Midway 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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 375AverageC$ 700FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 402AverageC$ 856FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 466AverageC$ 611FlexibilityNo 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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