Cheap flights from Florida Keys to Chicago from $62
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Florida Keys to Chicago departing on 8/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Spirit Airlines flights from Florida Keys to Chicago O'Hare Intl Airport
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Southwest flights from Florida Keys to Chicago O'Hare Intl Airport
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How to get the cheapest flight ticket from Florida Keys 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 February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Florida Keys averaging around $217.
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 $286. 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 Florida Keys because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $438.
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 Florida Keys in the evening is the least expensive time of day to depart. momondo users have found prices as low as $283 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $366. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Florida Keys to Chicago O'Hare Intl flight route?
Fly from Key West to Chicago O'Hare Intl for the best Florida Keys - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Florida Keys when booking 8 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $237 when searching 8 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Florida Keys for as low as $196 on momondo.
What cabin class options are available on Florida Keys to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Florida Keys 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.
How many flights depart from Florida Keys to Chicago O'Hare Intl Airport on average per day?
The number of flights available between Florida Keys and Chicago O'Hare Intl Airport is 38 per day as of June 2025. The most frequent departure time is 12:00PM, with 100% of daily flights leaving in the afternoon.
How many flights depart from Florida Keys to Chicago O'Hare Intl Airport on average per week?
The number of flights available between Florida Keys and Chicago O'Hare Intl Airport is 272 per week as of June 2025. The most frequent departure day is Thu, with 17% of weekly flights leaving on this day.
Cheap Florida Keys to Chicago O'Hare Intl Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Florida Keys to Chicago O'Hare Intl Airport
When did momondo last update prices for flights from Florida Keys to Chicago O'Hare Intl Airport?
Prices for flights from Florida Keys to Chicago O'Hare Intl Airport were last updated today.
How many operators does momondo search for flights from Florida Keys to Chicago O'Hare Intl Airport?
As of June 2025, there are 4 operators available to choose from for flights from Florida Keys to Chicago O'Hare Intl Airport.
How old do you have to be to fly from Florida Keys to Chicago O'Hare Intl 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 Florida Keys to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents you'll need for your trip to Chicago O'Hare Intl 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 Chicago O'Hare Intl 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 Florida Keys to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Florida Keys to Chicago O'Hare Intl Airport is Boeing 737-800 (20.32% of total bookings). The next most popular plane models are Airbus A321neo (8.60%), Boeing 737-900 (8.17%), and Boeing 737 MAX 8 (7.86%).
Best airlines flying from Florida Keys to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Florida Keys to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $224 | Free Cancellation | Rating 7.4 8,774 reviews | |||
| PriceFrom $289 | Free Cancellation | Rating 7.2 10,000 reviews |
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Why should I use momondo to find a flight deal from Florida Keys 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 Florida Keys to Chicago for you.
Can I find flights from Florida Keys to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Florida Keys with this policy.
How can momondo help me find flights from Florida Keys to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Florida Keys. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Florida Keys to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Florida Keys. 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.