Cheap flights from Chicago Midway Airport to Key West from $264
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Key West departing on 8/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago Midway Airport to Key West
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Key West?
In general, October is the cheapest month to fly from Chicago Midway Airport to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $225. If you are unable to visit Key West during the month of October, then departing from Chicago Midway Airport during the month July is also very affordable. Most momondo users find prices during this month for around $343.
What is the cheapest day to depart on your flight to Key West?
On average, the least expensive day to fly to Key West from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $359. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Key West for around $556.
When to book flights from Chicago Midway Airport to Key West
Cheap Chicago Midway Airport to Key West (MDW to EYW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Key West
How far is Chicago Midway to Key West by plane?
The distance between Chicago Midway and Key West is about 1237.6 mi. Typically, this will take 5h 08m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to Key West Airport?
Prices for flights from Chicago Midway Airport to Key West Airport refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to Key West Airport?
The number of operators available for flights from Chicago Midway Airport to Key West Airport is 1 as of July 2025.
How old do you have to be to fly from Chicago Midway Airport to Key West Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Key West Airport.
What documentation or ID do you need to fly to Key West Airport?
The required travel and health documents for your Key West Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Key West Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular airline from Chicago Midway Airport to Key West?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Key West is Delta (100% of total bookings).
Best airlines flying from Chicago Midway Airport to Key West
Compare and see reviews for airlines that fly from Chicago Midway Airport to Key West with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $248 | Free Cancellation | Rating 8.0 7,983 reviews |
Traveling to a place near Key West?
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Why should I use momondo to find a flight deal from Chicago to Key West?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Key West. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Key West with flexible booking policies on momondo?
Flights from Chicago to Key West with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Chicago to Key West?
Once all potential Chicago to Key West flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Chicago to Key West right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Key West, momondo offers a useful price alert feature which will track prices for flights to Key West from Chicago and alert you when they change.