Cheap flights from Florida to Chicago from $74
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 11/2. 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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Not ready to book? to track prices.Southwest flights from Florida to Chicago Midway Airport
Our best Southwest deals on Florida to Chicago Midway Airport flight tickets
Allegiant Air flights from Florida to Chicago Midway Airport
Our best Allegiant Air deals on Florida to Chicago Midway Airport flight tickets
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Use the filters below to find and compare flights from Florida to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 11/13
7:30 am-9:48 am
Nonstop2h 18m
Chicago Midway
Mon 11/16
1:08 pm-3:19 pm
Nonstop2h 11m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 10/23
6:07 pm-8:25 pm
Nonstop2h 18m
Chicago Midway
Mon 10/26
6:44 pm-8:55 pm
Nonstop2h 11m
Fort LauderdaleChicago
FLL Fort Lauderdale - MDW Chicago Midway
FLLMDW
Fort Lauderdale
Sat 11/7
7:15 am-9:25 am
Nonstop3h 10m
Chicago Midway
Sat 11/14
7:50 am-2:40 pm
2 stops5h 50m
Fort LauderdaleChicago
FLL Fort Lauderdale - MDW Chicago Midway
FLLMDW
Fort Lauderdale
Thu 11/5
2:22 pm-11:47 pm
1 stop10h 25m
Chicago Midway
Mon 11/9
6:08 am-3:24 pm
1 stop8h 16m
Fort LauderdaleChicago
FLL Fort Lauderdale - MDW Chicago Midway
FLLMDW
Fort Lauderdale
Fri 11/6
6:31 am-5:47 pm
1 stop12h 16m
Chicago Midway
Mon 11/9
6:08 am-3:24 pm
1 stop8h 16m
Fort LauderdaleChicago
FLL Fort Lauderdale - MDW Chicago Midway
FLLMDW
Fort Lauderdale
Thu 11/26
5:05 am-7:10 am
Nonstop3h 05m
Chicago Midway
Tue 12/1
1:15 pm-8:55 pm
2 stops6h 40m
Fort LauderdaleChicago
FLL Fort Lauderdale - MDW Chicago Midway
FLLMDW
Fort Lauderdale
Tue 11/10
8:40 am-5:47 pm
2 stops10h 07m
Chicago Midway
Wed 11/11
6:08 am-2:39 pm
1 stop7h 31m
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 11/13
1:39 pm-5:47 pm
2 stops28h 08m
Chicago Midway
Mon 11/16
1:08 pm-3:19 pm
Nonstop2h 11m
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Wed 1/13
12:20 pm-4:25 pm
1 stop5h 05m
Chicago Midway
Fri 1/29
6:00 am-12:13 pm
1 stop5h 13m
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Tue 1/12
8:20 am-12:33 pm
1 stop5h 13m
Chicago Midway
Fri 1/29
6:00 am-12:13 pm
1 stop5h 13m
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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Florida, with most prices found around $217. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Florida during the month February is also very affordable. Most momondo users find prices during this month for around $237.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Florida. The lowest ticket price found for a Saturday departure recently was $252. 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, Monday 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 $430.
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 $240 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $333. 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 from Florida to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Florida when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $298 when searching 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 $242 on momondo.
What cabin class options are available on Florida to Chicago Midway Airport flights?
There are 2 cabin classes available to choose from on Florida to Chicago Midway Airport 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, Delta, and Allegiant Air are the most popular carriers operating from Florida to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and JetBlue 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 74% 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?
20 flights are operational daily from Florida to Chicago Midway Airport as of October 2026. The most popular departure time for this route is 6:00AM, with 46% of flights per day taking off at noon.
How many flights depart from Florida to Chicago Midway Airport on average per week?
As of October 2026, 141 flights take off from Florida and land in Chicago Midway Airport each week. The most common flight departure day for this route is Tue, with 21% 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
Frequently asked questions about flying 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 October 2026, there are 5 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 Boeing 737 MAX 8, representing 19.18% of all bookings. The subsequent popular models are Airbus A321neo at 11.86%, Boeing 737-800 at 11.20%, and Airbus A320-100/200 at 10.69%.
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 $58 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $98 | Free Cancellation | Rating 7.8 8,646 reviews | |||
| PriceFrom $167 | Free Cancellation | Rating 7.9 4,224 reviews | |||
| PriceFrom $170 | Free Cancellation | Rating 7.1 3,048 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.