Cheap flights from Florida to Chicago from $37
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 5/21. 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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How to get the cheapest flight ticket from Florida 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 February is, on average, the cheapest month to fly to Chicago from Florida, with most prices found around $160. If you’re not able to fly to Chicago in February, then June is your next best option. Flight prices from Florida to Chicago during June average around $172.
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 Friday when prices can be found for as low as $255. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Florida to Chicago for around $387.
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 evening. Flights from Florida to Chicago during this time can be as low as $268. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $299.
What is the cheapest Florida to Chicago flight route?
Fly from Orlando Sanford Intl to Chicago Greater Rockford for the best Florida - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Florida when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $235 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Florida for as low as $186 on momondo.
What cabin class options are available on Florida to Chicago flights?
There are 4 cabin classes available to choose from on Florida to Chicago 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?
Spirit Airlines, Frontier, and United Airlines are the most popular carriers operating from Florida to Chicago
What airlines fly to Chicago?
Spirit Airlines, American Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Florida according to our data. Spirit Airlines is the first choice among our users, with 30% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Florida to Chicago on average per day?
As of April 2025, 202 flights take off from Florida and land in Chicago each day. The most common flight departure time for this route is 12:00PM, with 58% of daily flights taking off in the afternoon.
How many flights depart from Florida to Chicago on average per week?
1,419 flights are operational weekly from Florida to Chicago as of April 2025. The most popular departure day for this route is Thu, with 18% of flights per week taking off on this day.
Cheap Florida to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Florida to Chicago
When did momondo last update prices for flights from Florida to Chicago?
Prices for flights from Florida to Chicago were last updated today.
How many operators does momondo search for flights from Florida to Chicago?
As of April 2025, there are 6 operators available to choose from for flights from Florida to Chicago.
How old do you have to be to fly from Florida 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 Florida to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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. 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Florida to Chicago is Airbus A321neo (19.07% of total bookings). The next most popular plane models are Boeing 737-800 (18.35%), Airbus A320neo (17.76%), and Boeing 737 MAX 8 (7.94%).
Best airlines flying from Florida to Chicago
Compare and see reviews for airlines that fly from Florida to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $29 | Free Cancellation | Rating 6.0 3,281 reviews | |||
| PriceFrom $59 | Free Cancellation | Rating 6.3 7,926 reviews | |||
| PriceFrom $100 | Free Cancellation | Rating 7.3 734 reviews | |||
| PriceFrom $155 | Free Cancellation | Rating 8.0 4,280 reviews | |||
| PriceFrom $156 | Free Cancellation | Rating 7.4 8,667 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,917 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?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Florida.
Can I find flights from Florida to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Florida which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Florida to Chicago?
Once you have performed a search for Florida to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Florida 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 Florida and alert you when they change.