Cheap flights from Chicago to Regina
from 167 US$
Compare hundreds of airlines Chicago–Regina
The cheapest month is usually 2026-09 · 167 US$
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About this route
Compare flights from Chicago to Regina, a about 1,614 km route (around 2h 31m nonstop). We gather live prices from hundreds of airlines and agencies so you can find the cheapest and book on the official site, with no hidden fees. Direct flights are available. Airlines such as Air Canada, United Airlines operate this route.
When to buy and when to fly
Prices by date
Fares found by date — cheapest days in green.
How to get the best price
Airlines on this route
FAQ
What's the cheapest month to fly Chicago to Regina?
It's usually 2026-09, from 167 USD. Use the price calendar to compare other dates.
How long is the flight from Chicago to Regina?
A nonstop flight takes about 2h 31m and covers around 1,614 km. Connecting itineraries take longer.
Are there direct flights from Chicago to Regina?
Yes, this route has nonstop flights. Filter by "nonstop" to see them.
Which airlines fly from Chicago to Regina?
Air Canada, United Airlines operate this route, among others. Compare them all in the results.
When should I book Chicago–Regina flights?
As a rule of thumb, booking 3–8 weeks ahead and avoiding weekends and holidays tends to give the best prices. Use the calendar to spot the cheapest dates.
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Chicago → Regina · Live fares from 100+ sites — free, with no hidden fees.