Cheap flights from Florida to Chicago from $69
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 to Chicago departing on 9/7. 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 Florida to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Allegiant Air flights from Florida to Chicago Midway Airport
Our best Allegiant Air deals on Florida to Chicago Midway Airport flight tickets
Frontier flights from Florida to Chicago Midway Airport
Our best Frontier deals on Florida to Chicago Midway Airport flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Florida to Chicago Midway 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 Midway Airport?
The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Florida, with most prices found around $116. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Florida during the month July is also very affordable. Most momondo users find prices during this month for around $131.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Florida. The lowest ticket price found for a Thursday departure recently was $158. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Florida because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $287.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Florida in the evening is the least expensive time of day to depart. momondo users have found prices as low as $138 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $195. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Florida to Chicago Midway flight route?
Fly from Orlando to Chicago Midway for the best Florida - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Florida when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $202 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Florida for as low as $142 on momondo.
What cabin class options are available on Florida to Chicago Midway flights?
There are 1 cabin classes available to choose from on Florida to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Florida to Chicago Midway?
Southwest, Frontier, and Allegiant Air are the most popular carriers operating from Florida to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Florida according to our data. Southwest is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Florida to Chicago Midway Airport on average per day?
30 flights are operational daily from Florida to Chicago Midway Airport as of June 2025. The most popular departure time for this route is 6:00AM, with 44% of flights per day taking off at noon.
How many flights depart from Florida to Chicago Midway Airport on average per week?
As of June 2025, 214 flights take off from Florida and land in Chicago Midway Airport each week. The most common flight departure day for this route is Thu, with 15% of weekly flights taking off on this day.
Cheap Florida to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Florida to Chicago Midway Airport
When did momondo last update prices for flights from Florida to Chicago Midway Airport?
Prices for flights from Florida to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Florida to Chicago Midway Airport?
As of June 2025, there are 4 operators available to choose from for flights from Florida to Chicago Midway Airport.
How old do you have to be to fly from Florida to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Florida to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Florida to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Florida to Chicago Midway Airport is Airbus A320neo, representing 14.07% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.71%, Boeing 737-800 at 13.41%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 11.88%.
Best airlines flying from Florida to Chicago Midway Airport
Compare and see reviews for airlines that fly from Florida to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $67 | Free Cancellation | Rating 6.3 8,061 reviews | |||
| PriceFrom $70 | Free Cancellation | Rating 5.9 3,296 reviews | |||
| PriceFrom $138 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $162 | Free Cancellation | Rating 8.0 4,278 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 Florida to Chicago?
Finding the right flight to Chicago from Florida is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Florida to Chicago with flexible booking policies on momondo?
Flights from Florida 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 Florida 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 Florida.
I’m not ready to book a flight from Florida to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Florida. 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.