Cheap flights from Toronto to Chicago-Midway
Cheap return flights from Toronto to Chicago-Midway
Find the best deals
All prices shown are per person based on return flights only. Prices found in the last 48 hours.
Chicago-Midway flight facts
What you need to know
What are the cheapest airlines?
- Spirit Airlines
- Frontier Airlines
- American Airlines
These airlines usually offer the cheapest flights from Toronto to Chicago-Midway.
What airlines fly indirectly?
- United Airlines
- Delta Air Lines
- Southwest Airlines
These airlines fly from Toronto to Chicago-Midway, but you’ll have at least one layover.
How long is the flight?
1 hour 30 minutes
This is the shortest flight time from Toronto to Chicago-Midway.
Alternative flights from the UK to Chicago-Midway
Check out prices for other routes
Alternative flights from Toronto
You might find cheaper flights nearby
Today alone, Netflights has searched over five flights. 05 / Feb / 2026 is currently the lowest priced day of the year to fly the Toronto/Chicago-Midway route. There are around 35 flights on any given week from the UK to Chicago-Midway and the cheapest month to fly right now is February. Not suitable? Try running another search or viewing all cheap flight deals.
How to get cheap flights from Toronto to Chicago-Midway
Tips and advice from our flight experts
You've searched for flights from Toronto to Chicago-Midway. We've found 15 flights and compared them to give you the best offer. Spirit Airlines is, on average, the cheapest for this route. Look out for them! The cheapest offer we've found is a one-way ticket for Toronto to Chicago-Midway on 31/03/2026 at 19:05 for £35.
We've scanned hundreds of airfares from dozens of airlines across the globe. In total, we've found 5 airlines that operate the 700 km flight from Toronto to Chicago-Midway.
To find the best offers, consider booking 2-3 months in advance or look for last-minute deals. Spirit Airlines is a popular choice for this route, with an average flight duration of 1 hour 30 minutes. After selecting an offer, fill out your information and proceed to payment. Don't forget to check our flight + hotel service to book everything at once, saving time and money.
Other popular destinations near Chicago-Midway
Where other people are flying to
