Cheap flights from Chicago to Key West from $101
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 to Key West departing on 10/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Key West
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
American Airlines flights from Chicago to Key West
Our best American Airlines deals on Chicago to Key West flight tickets
Delta flights from Chicago to Key West
Our best Delta deals on Chicago to Key West flight tickets
See travel insights to Key West from
How to get the cheapest flight ticket from Chicago 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 typical price of a round-trip flight between Chicago and Key West?
What is the cheapest month to fly to Key West?
In general, October is the cheapest month to fly from Chicago to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $401. If you are unable to visit Key West during the month of October, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $404.
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 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 to Key West for around $556.
What is the cheapest time of day to depart on your flight to Key West?
According to our data, the cheapest time of day to fly to Key West is at noon. momondo users have found flights departing from Chicago to Key West at noon for as low as $338. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly in the evening, with an average ticket price of $822. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago to Key West flight route?
Fly from Chicago O'Hare Intl to Key West for the best Chicago - Key West flight prices
How far in advance should I book a flight to Key West?
You are more likely to see cheaper flights to Key West from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $441 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Chicago for as low as $368 on momondo.
What cabin class options are available on Chicago to Key West flights?
There are 3 cabin classes available to choose from on Chicago to Key West 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 Chicago to Key West flights?
No. A direct flight is the cheapest option for a flight between Chicago to Key West.
How have Chicago to Key West flight prices changed over time?
As of July 2025, prices for Chicago to Key West flights are approximately 60% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to Key West?
United Airlines, Delta, and American Airlines are the most popular carriers operating from Chicago to Key West
What airlines fly to Key West?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Key West from Chicago according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Key West. Keep in mind that there are 3 different airlines that fly to Key West on a routine basis, so you have a few additional options to choose from.
When to book flights from Chicago to Key West
Cheap Chicago to Key West (CHI to EYW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Key West
How far is Chicago to Key West by plane?
The distance between Chicago and Key West is about 1241.6 mi. 3h 16m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago to Key West Airport?
Prices for flights from Chicago to Key West Airport refresh daily.
How many operators does momondo search for flights from Chicago to Key West Airport?
The number of operators available for flights from Chicago to Key West Airport is 3 as of July 2025.
How old do you have to be to fly from Chicago to Key West Airport?
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 Chicago to Key West Airport.
What documentation or ID do you need to fly to Key West Airport?
The travel and health documents you'll need for your trip to Key West Airport 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 Key West Airport. 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 Chicago to Key West?
Based on momondo bookings for flights between Chicago and Key West, the leading plane model is Embraer 170, making up 43.52% of the total bookings. Other popular models include Boeing 737-700 with 34.58%, Embraer 175 with 9.51%, and Embraer 175 (Enhanced Winglets) with 4.61%.
What is the most popular airline from Chicago to Key West?
Based on momondo bookings for flights between Chicago and Key West, the leading airline is American Airlines, making up 47% of the total bookings. Other popular airlines include United Airlines with 45% and Delta with 8%.
Best airlines flying from Chicago to Key West
Compare and see reviews for airlines that fly from Chicago to Key West with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $216 | Free Cancellation | Rating 8.0 7,983 reviews | |||
| PriceFrom $264 | Free Cancellation | Rating 7.4 8,861 reviews | |||
| PriceFrom $285 | Free Cancellation | Rating 7.2 10,000 reviews |
Traveling to a place near Key West?
Book flights to Key West if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Key West?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Key West. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to Key West with flexible booking policies on momondo?
momondo does allow users to show only those flights to Key West from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Key West?
momondo provides multiple filters to help you find the best flight to Key West from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Key West right now. Can momondo alert me if prices change?
Price alerts on flights to Key West from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.