Cheap flights from New York to Chicago-Midway
Cheap return flights from New York 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
- Southwest Airlines
These airlines usually offer the cheapest flights from New York to Chicago-Midway.
What airlines fly indirectly?
- American Airlines
- Delta Air Lines
- United Airlines
These airlines fly from New York to Chicago-Midway, but you’ll have at least one layover.
How long is the flight?
2 hours 30 minutes
This is the shortest flight time from New York to Chicago-Midway.
Alternative flights from the UK to Chicago-Midway
Check out prices for other routes
Alternative flights from New York
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 New York/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 New York to Chicago-Midway
Tips and advice from our flight experts
You've searched for flights from New York to Chicago-Midway. We found 25 flights and compared them to give you the best offer. Southwest Airlines is usually the cheapest for this route, so keep an eye on them. The cheapest offer we've found is a one-way ticket for £48 from New York to Chicago-Midway on 10/06/2026 at 19:20.
We've scanned hundreds of airfares from dozens of airlines across the globe. In total, we've found 10 airlines that operate the 1,200 km flight from New York to Chicago-Midway.
To find the best offers, book at least 3-4 weeks in advance. Consider traveling during off-peak seasons. Southwest Airlines is a popular choice for this route, with an average flight duration of 2 hours 30 minutes. After selecting an offer, fill out your information and proceed to payment. Consider booking a hotel with us or using our flight + hotel service to save time and money.
Other popular destinations near Chicago-Midway
Where other people are flying to
