Cheap Flights From Regina Intl. (YQR) To O'Hare Intl. (ORD)

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Cheapest Flights from Regina (YQR) to Chicago (ORD)

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $435 round trip and CA $247 one way. Prices and availability subject to change. Additional terms may apply.

Thu, Sep. 4 - Thu, Sep. 11
YQR
Regina
ORD
Chicago
CA $435 Roundtrip, found 4 days ago
CA $435
Roundtrip
found 4 days ago
Select WestJet flight, departing Thu, Sep. 4 from Regina to Chicago, returning Thu, Sep. 11, priced at CA $435 found 4 days ago
Mon, Sep. 22 - Wed, Sep. 24
YQR
Regina
ORD
Chicago
CA $435 Roundtrip, found 2 days ago
CA $435
Roundtrip
found 2 days ago
Select WestJet flight, departing Mon, Sep. 22 from Regina to Chicago, returning Wed, Sep. 24, priced at CA $435 found 2 days ago
Fri, Sep. 26 - Mon, Oct. 6
YQR
Regina
ORD
Chicago
CA $467 Roundtrip, found 7 hours ago
CA $467
Roundtrip
found 7 hours ago
Select WestJet flight, departing Fri, Sep. 26 from Regina to Chicago, returning Mon, Oct. 6, priced at CA $467 found 7 hours ago
Wed, Aug. 27 - Wed, Sep. 3
YQR
Regina
ORD
Chicago
CA $481 Roundtrip, found 1 day ago
CA $481
Roundtrip
found 1 day ago
Select WestJet flight, departing Wed, Aug. 27 from Regina to Chicago, returning Wed, Sep. 3, priced at CA $481 found 1 day ago
Fri, Sep. 5 - Sun, Sep. 7
YQR
Regina
ORD
Chicago
CA $484 Roundtrip, found 2 days ago
CA $484
Roundtrip
found 2 days ago
Select WestJet flight, departing Fri, Sep. 5 from Regina to Chicago, returning Sun, Sep. 7, priced at CA $484 found 2 days ago
Thu, Sep. 4 - Thu, Sep. 11
YQR
Regina
ORD
Chicago
CA $488 Roundtrip, found 4 days ago
CA $488
Roundtrip
found 4 days ago
Select WestJet flight, departing Thu, Sep. 4 from Regina to Chicago, returning Thu, Sep. 11, priced at CA $488 found 4 days ago
Sat, Sep. 20 - Mon, Oct. 6
YQR
Regina
ORD
Chicago
CA $489 Roundtrip, found 6 days ago
CA $489
Roundtrip
found 6 days ago
Select WestJet flight, departing Sat, Sep. 20 from Regina to Chicago, returning Mon, Oct. 6, priced at CA $489 found 6 days ago
Thu, Sep. 25 - Wed, Oct. 1
YQR
Regina
ORD
Chicago
CA $521 Roundtrip, found 9 hours ago
CA $521
Roundtrip
found 9 hours ago
Select WestJet flight, departing Thu, Sep. 25 from Regina to Chicago, returning Wed, Oct. 1, priced at CA $521 found 9 hours ago
Thu, Aug. 28 - Sun, Aug. 31
YQR
Regina
ORD
Chicago
CA $525 Roundtrip, found 4 days ago
CA $525
Roundtrip
found 4 days ago
Select WestJet flight, departing Thu, Aug. 28 from Regina to Chicago, returning Sun, Aug. 31, priced at CA $525 found 4 days ago
Fri, Sep. 5 - Sun, Sep. 7
YQR
Regina
ORD
Chicago
CA $530 Roundtrip, found 2 days ago
CA $530
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Sep. 5 from Regina to Chicago, returning Sun, Sep. 7, priced at CA $530 found 2 days ago

O'Hare Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to Chicago (ORD)
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Frequently asked questions

What airlines fly from Regina Airport to O'Hare Airport?
When traveling from Regina Intl. Airport (YQR) to ORD, it's best to plan ahead — no direct flights are currently available. Booking well in advance should help you get the most convenient route and price.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Regina (YQR)

Travelers at YQR love to visit these top cities. Roam to the top destinations from Regina (YQR) today with the cheap prices from Travelocity!

Popular Flight Routes from Chicago (ORD)

Travelers at ORD love to visit these top cities. Roam to the top destinations from Chicago(ORD) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.