Cheap flights from Key West to Chicago from $177
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Key West to Chicago departing on 7/22. 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 Key West to Chicago
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 day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $329. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Key West to Chicago for around $939.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Key West to Chicago during this time can be as low as $359. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $507.
What is the cheapest Key West to Chicago flight route?
Fly from Key West to Chicago O'Hare Intl for the best Key West - Chicago flight prices
What cabin class options are available on Key West to Chicago flights?
There are 4 cabin classes available to choose from on Key West to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Key West to Chicago flights?
You could potentially save up to 10% on your flight if you consider stops on a Key West to Chicago flight.
How have Key West to Chicago flight prices changed over time?
When to book flights from Key West to Chicago
Cheap Key West to Chicago (EYW to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Key West to Chicago
How far is Key West to Chicago by plane?
Chicago is 1241.6 mi away from Key West. In terms of flight time, this usually takes a little over 4h 35m.
When did momondo last update prices for flights from Key West Airport to Chicago?
Prices for flights from Key West Airport to Chicago refresh daily.
How many operators does momondo search for flights from Key West Airport to Chicago?
As of July 2025, there are 2 operators available to choose from for flights from Key West Airport to Chicago.
How old do you have to be to fly from Key West Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Key West Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Key West to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Key West to Chicago is Embraer 170 (59.09% of total bookings). The next most popular plane models are Boeing 737-700 (18.18%), Airbus A319 (13.64%), and Embraer 175 (9.09%).
What is the most popular airline from Key West to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Key West to Chicago is United Airlines (41% of total bookings). The next most popular airlines are American Airlines (38%) and Delta (21%).
Best airlines flying from Key West to Chicago
Compare and see reviews for airlines that fly from Key West to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $224 | Free Cancellation | Rating 7.4 8,858 reviews | |||
| PriceFrom $259 | Free Cancellation | Rating 7.2 10,000 reviews |
Traveling to a place near Chicago?
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Why should I use momondo to find a flight deal from Key West to Chicago?
It is quick and easy to find Key West to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Key West to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Key West on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Key West to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Key West. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Key West to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Key West. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.