HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$48+ Cheap flights from Florida Keys to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Florida Keys to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Florida Keys to Midway

Keep the following information in mind while searching for Florida Keys to Midway flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$92
(Trip.com)

One-way from

$48
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$536
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
Search Deals
From Florida Keys to Chicago Midway
Search Deals
One-way flight from Florida Keys to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

Find flight deals from Florida Keys to Midway

Cheapest flights from Florida Keys to Midway
Explore the most affordable flight options available from Florida Keys to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Trip.com deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/512:42 pmMIA - MDW
Nonstop3h 31mFrontier
Sun 3/97:25 amMDW - MIA
Nonstop3h 12mFrontier
Deal found 2/19$92
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/196:10 pmMIA - MDW
1 stop5h 13mDelta
Tue 3/252:55 pmMDW - MIA
1 stop5h 26mDelta
Deal found 2/20$218
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/17:25 amMIA - MDW
1 stop7h 15mSouthwest
Tue 4/15:35 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 2/20$229
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/246:13 pmEYW - MDW
1 stop5h 13mDelta
Mon 4/286:04 amMDW - EYW
1 stop7h 01mDelta
Deal found 2/20$329

Find flights from Florida Keys to Midway within your budget

Customize your flight search to find flights from Florida Keys to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Florida Keys

Fly to

Midway

Route

Depart

Return

Price

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 3/5

12:42 pm-3:13 pm

Nonstop3h 31m

Chicago Midway

Sun 3/9

7:25 am-11:37 am

Nonstop3h 12m

$92

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 3/19

6:10 pm-10:23 pm

1 stop5h 13m

Chicago Midway

Tue 3/25

2:55 pm-9:21 pm

1 stop5h 26m

$218

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 4/1

7:25 am-1:40 pm

1 stop7h 15m

Chicago Midway

Tue 4/1

5:35 pm-9:35 pm

Nonstop3h 00m

$229

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/24

6:13 pm-10:26 pm

1 stop5h 13m

Chicago Midway

Mon 4/28

6:04 am-2:05 pm

1 stop7h 01m

$329

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 4/17

1:03 pm-3:29 pm

Nonstop3h 26m

$48

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 3/26

8:20 am-10:35 am

Nonstop3h 15m

$90

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 5/17

8:05 am-12:30 pm

1 stop5h 25m

$109

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 4/15

10:00 am-4:08 pm

1 stop7h 08m

$131

MiamiChicago

MIA - MDW

MIAMDW

Miami

Mon 3/24

8:59 am-5:46 pm

3 stops33h 47m

$205

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 3/19

6:15 pm-8:45 am

2 stops15h 30m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Best time to book a flight from Florida Keys to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Florida Keys with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Florida Keys to Midway

Get recent, data-driven insights about flights from Florida Keys to Midway including ideal travel times, pricing trends, and more.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated February 20, 2025.
Read through reviews of airlines operating flights from Florida Keys to Chicago, such as Southwest, Delta and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Florida Keys to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $48 on Frontier. Other airlines that offer cheap prices include Southwest from $90 and Delta from $109 one-way.

  • Can I find deals for flights from Florida Keys to Midway that include hotel bookings?

    Yes. In addition to deals on Florida Keys to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida Keys to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida Keys to Midway.

  • Can I find deals for business class flights from Florida Keys to Midway?

    Yes. Cheapflights offers flight deals from Florida Keys to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Florida Keys to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Florida Keys to Chicago Midway Airport (average of $160). Flying from Florida Keys to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Florida Keys?

Book flights to Florida Keys if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Florida Keys to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to Midway flights
Jacksonville to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Fort Lauderdale to Midway flights
Sarasota to O'Hare Intl flights
Tampa to Midway flights
Orlando to Midway flights
Jacksonville to Midway flights
West Palm Beach to Midway flights
Pensacola to O'Hare Intl flights
Fort Myers to Midway flights
Pensacola to Midway flights
Sarasota to Midway flights
Panama City to O'Hare Intl flights
Valparaiso to O'Hare Intl flights
Gainesville to O'Hare Intl flights
St Petersburg to Rockford flights
Valparaiso to Midway flights
Melbourne to O'Hare Intl flights
Tallahassee to O'Hare Intl flights
Panama City to Midway flights
Daytona Beach to O'Hare Intl flights
Gainesville to Midway flights
Daytona Beach to Midway flights
Tallahassee to Midway flights
Orlando Sanford Intl to Rockford flights
Melbourne to Midway flights
Key West to O'Hare Intl flights
Orlando to Rockford flights
Fort Lauderdale to Rockford flights
Punta Gorda to Rockford flights
Key West to Midway flights
Fort Myers to Rockford flights
Valdosta to O'Hare Intl flights
Tampa to Rockford flights
Pensacola to Rockford flights
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.