Cheap flights from Milwaukee to Chicago
Cheap return flights from Milwaukee to Chicago
Find the best deals
All prices shown are per person based on return flights only. Prices found in the last 48 hours.
Chicago flight facts
What you need to know
What are the cheapest airlines?
- Southwest Airlines
- United Airlines
- American Airlines
These airlines usually offer the cheapest flights from Milwaukee to Chicago.
What airlines fly indirectly?
- Delta Airlines
- Alaska Airlines
- Spirit Airlines
These airlines fly from Milwaukee to Chicago, but you’ll have at least one layover.
How long is the flight?
1 hour
This is the shortest flight time from Milwaukee to Chicago.
Alternative flights from the UK to Chicago
Check out prices for other routes
Alternative flights from Milwaukee
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 Milwaukee/Chicago route. There are around 35 flights on any given week from the UK to Chicago 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 Milwaukee to Chicago
Tips and advice from our flight experts
You've searched for flights from Milwaukee to Chicago. We've found 15 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 Milwaukee to Chicago on 20/07/2026 at 19:05 for £57.
We've scanned hundreds of airfares from dozens of airlines across the globe. In total, we've found 5 airlines that operate the 150 km flight from Milwaukee to Chicago.
To find the best offers, book at least 2-3 months in advance. Consider flying during off-peak seasons. Southwest Airlines is a popular choice for this route, with an average flight duration of 1 hour. After selecting an offer, fill out your information and proceed to payment. Don't forget to check our flight + hotel service to save time and money!
Other popular destinations near Chicago
Where other people are flying to
