Cheap flights from Key West to Chicago from $105
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 1/8. 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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Fly from
Fly to
Route
Depart
Return
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Wed 10/28
10:04 am-8:56 am
2 stops23h 52m
Chicago O'Hare Intl
Sat 10/31
9:51 am-11:19 am
1 stop24h 28m
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sun 11/1
10:59 am-8:46 am
1 stop22h 47m
Chicago O'Hare Intl
Mon 11/9
7:50 pm-9:24 am
2 stops36h 34m
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sun 11/1
10:59 am-8:46 am
1 stop22h 47m
Chicago O'Hare Intl
Mon 11/9
7:50 pm-9:24 am
2 stops36h 34m
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sun 11/1
7:18 pm-12:01 am
1 stop5h 43m
Chicago O'Hare Intl
Mon 11/9
7:30 am-11:54 am
Nonstop3h 24m
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sun 11/1
7:18 pm-12:01 am
1 stop5h 43m
Chicago O'Hare Intl
Mon 11/9
5:19 am-1:03 pm
1 stop6h 44m
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Fri 10/30
10:59 am-8:46 am
1 stop22h 47m
Chicago O'Hare Intl
Sun 11/1
7:55 am-12:19 pm
2 stops27h 24m
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sat 10/24
10:04 am-6:31 pm
2 stops9h 27m
Chicago O'Hare Intl
Wed 10/28
9:51 am-10:19 am
1 stop23h 28m
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sat 10/31
10:04 am-6:16 pm
2 stops9h 12m
Chicago O'Hare Intl
Sun 11/1
9:51 am-10:19 am
1 stop23h 28m
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Sat 10/31
1:44 pm-7:55 pm
1 stop7h 11m
Chicago O'Hare Intl
Sun 11/1
12:10 pm-4:32 pm
Nonstop3h 22m
Key WestChicago
EYW Key West - ORD Chicago O'Hare Intl
EYWORD
Key West
Fri 10/30
5:28 pm-11:33 pm
1 stop7h 05m
Chicago O'Hare Intl
Sun 11/1
12:10 pm-4:32 pm
Nonstop3h 22m
See travel insights to Chicago from
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 month to fly to Chicago?
The month of September is, on average, the cheapest month to fly to Chicago from Key West, with most prices found around $0. If you’re not able to fly to Chicago in September, then March is your next best option. Flight prices from Key West to Chicago during March average around $0.
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 Wednesday when prices can be found for as low as $339. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Key West to Chicago for around $856.
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 in the morning. Flights from Key West to Chicago during this time can be as low as $353. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $457.
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 47% on your flight if you consider stops on a Key West to Chicago flight.
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
Frequently asked questions about flying 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 3h 25m.
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 October 2026, there is 1 operator 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 (35.71% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (21.43%), Embraer 175 (14.29%), and Boeing 737-700 (7.14%).
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 American Airlines (100% of total bookings).
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 $319 | Free Cancellation | Rating 7.0 12,152 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
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.