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Cheap flights from Regina to Chicago from C$ 220

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 26/7. Fares are subject to change and may not be available on all flights or dates of travel.
YQR — CHI
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 431

One-way from

C$ 220

Popular in

November

Cheapest in

May

Average price

C$ 587
WestJet
  • WestJet
  • 15/7-22/7
  • 2 total stops
  • 34h 11m total
  • Regina to Chicago
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26/7
  • 26/7
  • 1 total stop
  • 6h 12m total
  • Regina to Chicago
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Highest demand for flights based on searches. 16% potential increase in price (C$ 174 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 34 potential savings vs. average RT price).
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Average for round-trip flights in June 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 12 June 2025.

Tue 15/710:05 a.m.YQR - ORD
1 stop25h 34mWestJet
Tue 22/75:30 p.m.ORD - YQR
1 stop8h 37mWestJet
Deal found 11/6C$ 431
Fri 25/76:55 a.m.YQR - ORD
1 stop8h 49mMultiple Airlines
Mon 28/76:15 p.m.ORD - YQR
1 stop23h 15mMultiple Airlines
Deal found 10/6C$ 439
Fri 25/77:10 p.m.YQR - ORD
1 stop12h 59mAir Canada
Mon 28/78:25 p.m.ORD - YQR
1 stop15h 05mAir Canada
Deal found 11/6C$ 495
Sat 26/79:45 a.m.YQR - ORD
1 stop9h 20mUnited Airlines
Sat 2/84:20 p.m.ORD - YQR
1 stop6h 16mUnited Airlines
Deal found 10/6C$ 514
Sun 20/79:00 a.m.YQR - ORD
1 stop6h 44mDelta
Sat 26/78:30 a.m.ORD - YQR
1 stop9h 00mDelta
Deal found 10/6C$ 536
Tue 15/710:15 a.m.YQR - MDW
1 stop6h 24mDelta
Tue 22/79:24 a.m.MDW - YQR
1 stop8h 06mDelta
Deal found 11/6C$ 715
Fri 4/76:55 a.m.YQR - MDW
2 stops9h 45mWestJet
Sun 6/77:21 p.m.MDW - YQR
1 stop22h 09mWestJet
Deal found 11/6C$ 924

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 12 June 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

Tue 15/7

10:05 a.m.-12:39 p.m.

1 stop25h 34m

Chicago O'Hare Intl

Tue 22/7

5:30 p.m.-1:07 a.m.

1 stop8h 37m

C$ 431

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 25/7

6:55 a.m.-4:44 p.m.

1 stop8h 49m

Chicago O'Hare Intl

Mon 28/7

6:15 p.m.-4:30 p.m.

1 stop23h 15m

C$ 439

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 25/7

7:10 p.m.-9:09 a.m.

1 stop12h 59m

Chicago O'Hare Intl

Mon 28/7

8:25 p.m.-10:30 a.m.

1 stop15h 05m

C$ 495

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 26/7

9:45 a.m.-8:05 p.m.

1 stop9h 20m

Chicago O'Hare Intl

Sat 2/8

4:20 p.m.-9:36 p.m.

1 stop6h 16m

C$ 514

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 20/7

9:00 a.m.-4:44 p.m.

1 stop6h 44m

Chicago O'Hare Intl

Sat 26/7

8:30 a.m.-4:30 p.m.

1 stop9h 00m

C$ 536

ReginaChicago

YQR - MDW

YQRMDW

Regina

Tue 15/7

10:15 a.m.-5:39 p.m.

1 stop6h 24m

Chicago Midway

Tue 22/7

9:25 a.m.-4:30 p.m.

2 stops8h 05m

C$ 715

ReginaChicago

YQR - MDW

YQRMDW

Regina

Fri 4/7

6:55 a.m.-5:40 p.m.

2 stops9h 45m

Chicago Midway

Sun 6/7

7:21 p.m.-4:30 p.m.

1 stop22h 09m

C$ 924

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 26/7

10:15 a.m.-5:27 p.m.

1 stop6h 12m

C$ 220

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 29/7

6:55 a.m.-4:44 p.m.

1 stop8h 49m

C$ 228

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 21/11

6:00 a.m.-2:51 p.m.

1 stop8h 51m

C$ 252

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 14 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$ 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 12 June 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 12 June 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines and WestJet from Regina to Chicago to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,946 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,946 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,868 reviews
Delta
8.0
Very good
7,946 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Canada
7.1
Good
9,537 reviews
Delta
8.0
Very good
7,946 reviews
Check prices

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    WestJet, at C$ 431, was found to be the cheapest airline from Regina to Chicago.Alternate airlines to your destination round-trip include Air Canada and United Airlines. WestJet is 31% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Regina to Chicago one-way?

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as C$ 228. However, be on the lookout for offers from Air Canada and Delta, as they are both options that can get you from Regina to Chicago for a low price.

  • 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.
Regina to O'Hare Intl flights
Saskatoon 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 392AverageC$ 777FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 399AverageC$ 707FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 459AverageC$ 582FlexibilityNo 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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