Cheap flights from Key West to Chicago from $188
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 7/18. 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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United Airlines flights from Key West to Chicago O'Hare Intl Airport
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American Airlines flights from Key West to Chicago O'Hare Intl Airport
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How to get the cheapest flight ticket from Key West to Chicago O'Hare Intl Airport
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 Chicago O'Hare Intl Airport?
The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Key West averaging around $289.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Sunday is the most expensive day to depart from Key West because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $939.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Key West at noon is the least expensive time of day to depart. momondo users have found prices as low as $353 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $507. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Key West to Chicago O'Hare Intl flight route?
Fly from Key West to Chicago O'Hare Intl for the best Key West - Chicago O'Hare Intl flight prices
What cabin class options are available on Key West to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Key West to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?
You could potentially save up to 19% on your flight if you consider stops on a Key West to Chicago O'Hare Intl Airport flight.
What is the cheapest airline that flies from Key West to Chicago O'Hare Intl?
Delta, American Airlines, and Alaska Airlines are the most popular carriers operating from Key West to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Key West according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
When to book flights from Key West to Chicago O'Hare Intl Airport
Cheap Key West to Chicago O'Hare Intl Airport (EYW to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Key West to Chicago O'Hare Intl Airport
How far is Key West to Chicago O'Hare Intl by plane?
Chicago O'Hare Intl is 1252.7 mi away from Key West. Typically, this will take 3h 35m by plane in normal conditions.
When did momondo last update prices for flights from Key West Airport to Chicago O'Hare Intl Airport?
Prices for flights from Key West Airport to Chicago O'Hare Intl Airport refresh daily.
How many operators does momondo search for flights from Key West Airport to Chicago O'Hare Intl Airport?
The number of operators available for flights from Key West Airport to Chicago O'Hare Intl Airport is 3 as of June 2025.
How old do you have to be to fly from Key West Airport to Chicago O'Hare Intl Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Key West Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Key West to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Key West to Chicago O'Hare Intl Airport is Embraer 170 (53.85% of total bookings). The next most popular plane models are Boeing 737-700 (26.92%), Airbus A319 (11.54%), and Embraer 175 (7.69%).
What is the most popular airline from Key West to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Key West and Chicago O'Hare Intl Airport, the leading airline is American Airlines, making up 50% of the total bookings. Other popular airlines include United Airlines with 36% and Delta with 14%.
Best airlines flying from Key West to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Key West to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $224 | Free Cancellation | Rating 7.4 8,810 reviews | |||
| PriceFrom $259 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $278 | Free Cancellation | Rating 8.0 7,964 reviews |
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Why should I use momondo to find a flight deal from Key West to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Key West to Chicago for you.
Can I find flights from Key West to Chicago with flexible booking policies on momondo?
Flights from Key West to Chicago 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 Key West to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Key West.
I’m not ready to book a flight from Key West to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Key West and alert you when they change.