How does KAYAK find such low prices on flights from Florida to Chicago Midway Airport?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Florida to Chicago Midway Airport.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Florida to Chicago Midway Airport?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Florida is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Florida to Chicago Midway Airport?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Florida with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Florida to Chicago Midway Airport?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Florida up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$76 CHEAP FLIGHTS from Florida to Chicago Midway (MDW)

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals

Cheap Flights from Florida to Midway

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Florida to Midway

Sun, Nov 22 - Mon, Nov 30

6:30 am - 8:54 amVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 24mnonstop

6:51 pm - 8:56 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 05mnonstop

$120Allegiant Air

Fri, Oct 16 - Mon, Oct 26

6:12 pm - 8:30 pmVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 18mnonstop

6:44 pm - 8:55 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 11mnonstop

$127Allegiant Air

Wed, Nov 11 - Sat, Nov 14

3:23 pm - 11:47 pmFLL Fort Lauderdale-MDW Chicago Midway

9h 24m1 stop Atlanta Hartsfield-Jackson

7:25 am - 3:24 pmMDW Chicago Midway-FLL Fort Lauderdale

6h 59m1 stop Atlanta Hartsfield-Jackson

$162Frontier

Sat, Oct 31 - Tue, Nov 3

6:39 am - 5:47 pmFLL Fort Lauderdale-MDW Chicago Midway

12h 08m1 stop Atlanta Hartsfield-Jackson

6:16 am - 2:15 pmMDW Chicago Midway-FLL Fort Lauderdale

6h 59m1 stop Atlanta Hartsfield-Jackson

$162Frontier

Sat, Nov 7 - Tue, Nov 10

2:55 pm - 5:10 pmFLL Fort Lauderdale-MDW Chicago Midway

3h 15mnonstop

6:20 pm - 10:20 pmMDW Chicago Midway-FLL Fort Lauderdale

3h 00mnonstop

$175Southwest

Sat, Nov 7 - Tue, Nov 10

2:55 pm - 5:10 pmFLL Fort Lauderdale-MDW Chicago Midway

3h 15mnonstop

6:20 pm - 10:20 pmMDW Chicago Midway-FLL Fort Lauderdale

3h 00mnonstop

$175Southwest

Sat, Nov 21 - Tue, Nov 24

6:35 pm - 10:54 pmFLL Fort Lauderdale-MDW Chicago Midway

5h 19m1 stop Atlanta Hartsfield-Jackson

9:30 am - 3:45 pmMDW Chicago Midway-FLL Fort Lauderdale

5h 15m1 stop Detroit Metropolitan Wayne County

$217Delta

Tue, Dec 1 - Tue, Dec 8

6:35 pm - 10:54 pmFLL Fort Lauderdale-MDW Chicago Midway

5h 19m1 stop Atlanta Hartsfield-Jackson

5:12 pm - 12:45 amMDW Chicago Midway-FLL Fort Lauderdale

6h 33m1 stop Atlanta Hartsfield-Jackson

$217Delta

Thu, Oct 29 - Sat, Oct 31

8:36 pm - 1:36 pmJAX Jacksonville-MDW Chicago Midway

18h 00m1 stop Knoxville McGhee Tyson

7:25 am - 6:28 pmMDW Chicago Midway-JAX Jacksonville

10h 03m1 stop Atlanta Hartsfield-Jackson

$219Multiple Airlines

Thu, Oct 29 - Wed, Nov 4

8:36 pm - 1:36 pmJAX Jacksonville-MDW Chicago Midway

18h 00m1 stop Knoxville McGhee Tyson

6:16 am - 6:08 pmMDW Chicago Midway-JAX Jacksonville

10h 52m1 stop Atlanta Hartsfield-Jackson

$219Multiple Airlines

Recent last minute flight deals from Florida to Midway

Fri, Oct 2 - Mon, Oct 5

6:16 pm - 8:34 pmVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 18mnonstop

9:02 pm - 11:13 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 11mnonstop

$196Allegiant Air

Thu, Oct 1 - Wed, Oct 28

6:49 am - 5:46 pmFLL Fort Lauderdale-MDW Chicago Midway

11h 57m1 stop Atlanta Hartsfield-Jackson

6:16 am - 2:21 pmMDW Chicago Midway-FLL Fort Lauderdale

7h 05m1 stop Atlanta Hartsfield-Jackson

$257Frontier

Wed, Sep 30 - Fri, Oct 30

9:30 am - 5:51 pmMCO Orlando-MDW Chicago Midway

9h 21m1 stop Atlanta Hartsfield-Jackson

6:16 am - 5:24 pmMDW Chicago Midway-MCO Orlando

10h 08m1 stop Atlanta Hartsfield-Jackson

$280Frontier

Sat, Oct 3 - Sat, Oct 10

12:52 pm - 5:51 pmTPA Tampa-MDW Chicago Midway

5h 59m1 stop Atlanta Hartsfield-Jackson

6:21 am - 6:24 pmMDW Chicago Midway-TPA Tampa

11h 03m1 stop Atlanta Hartsfield-Jackson

$290Frontier

Thu, Oct 1 - Wed, Oct 28

6:35 am - 8:45 amFLL Fort Lauderdale-MDW Chicago Midway

3h 10mnonstop

5:55 pm - 9:55 pmMDW Chicago Midway-FLL Fort Lauderdale

3h 00mnonstop

$332Southwest

Thu, Oct 1 - Wed, Oct 28

7:05 pm - 11:05 pmFLL Fort Lauderdale-MDW Chicago Midway

5h 00m1 stop Lambert-St Louis

5:55 pm - 9:55 pmMDW Chicago Midway-FLL Fort Lauderdale

3h 00mnonstop

$342Southwest

Tue, Sep 29 - Tue, Sep 29

8:20 am - 12:39 pmTPA Tampa-MDW Chicago Midway

5h 19m1 stop Detroit Metropolitan Wayne County

5:11 pm - 12:19 amMDW Chicago Midway-TPA Tampa

6h 08m1 stop Atlanta Hartsfield-Jackson

$413Delta

Tue, Sep 29 - Tue, Sep 29

6:20 am - 9:49 amTPA Tampa-MDW Chicago Midway

4h 29m1 stop Atlanta Hartsfield-Jackson

5:11 pm - 12:19 amMDW Chicago Midway-TPA Tampa

6h 08m1 stop Atlanta Hartsfield-Jackson

$413Delta

Sun, Oct 4 - Thu, Oct 8

9:43 pm - 12:06 pmJAX Jacksonville-MDW Chicago Midway

15h 23m1 stop Knoxville McGhee Tyson

1:12 pm - 6:31 pmMDW Chicago Midway-JAX Jacksonville

28h 19m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson

$439Multiple Airlines

Sun, Oct 4 - Sun, Oct 11

9:43 pm - 12:06 pmJAX Jacksonville-MDW Chicago Midway

15h 23m1 stop Knoxville McGhee Tyson

6:24 am - 5:25 pmMDW Chicago Midway-JAX Jacksonville

10h 01m1 stop Atlanta Hartsfield-Jackson

$446Multiple Airlines

Recent direct flight deals from Florida to Midway

Sun, Nov 22 - Mon, Nov 30

6:30 am - 8:54 amVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 24mnonstop

6:51 pm - 8:56 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 05mnonstop

$120Allegiant Air

Fri, Oct 16 - Mon, Oct 26

6:12 pm - 8:30 pmVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 18mnonstop

6:44 pm - 8:55 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 11mnonstop

$127Allegiant Air

Fri, Oct 16 - Fri, Oct 23

6:12 pm - 8:30 pmVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 18mnonstop

9:15 pm - 11:26 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 11mnonstop

$127Allegiant Air

Fri, Oct 23 - Mon, Oct 26

6:07 pm - 8:25 pmVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 18mnonstop

6:44 pm - 8:55 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 11mnonstop

$138Allegiant Air

Sat, Nov 7 - Tue, Nov 10

2:55 pm - 5:10 pmFLL Fort Lauderdale-MDW Chicago Midway

3h 15mnonstop

6:20 pm - 10:20 pmMDW Chicago Midway-FLL Fort Lauderdale

3h 00mnonstop

$175Southwest

Sat, Nov 7 - Tue, Nov 10

2:55 pm - 5:10 pmFLL Fort Lauderdale-MDW Chicago Midway

3h 15mnonstop

6:20 pm - 10:20 pmMDW Chicago Midway-FLL Fort Lauderdale

3h 00mnonstop

$175Southwest

Tue, Oct 27 - Tue, Oct 27

6:50 am - 9:00 amFLL Fort Lauderdale-MDW Chicago Midway

3h 10mnonstop

12:15 pm - 4:10 pmMDW Chicago Midway-FLL Fort Lauderdale

2h 55mnonstop

$183Southwest

Tue, Nov 24 - Wed, Nov 25

5:46 pm - 7:47 pmMCO Orlando-MDW Chicago Midway

3h 01mnonstop

8:42 pm - 12:25 amMDW Chicago Midway-MCO Orlando

2h 43mnonstop

$254Frontier

Wed, Nov 25 - Sat, Nov 28

5:46 pm - 7:47 pmMCO Orlando-MDW Chicago Midway

3h 01mnonstop

8:42 pm - 12:25 amMDW Chicago Midway-MCO Orlando

2h 43mnonstop

$254Frontier

Wed, Dec 23 - Wed, Dec 30

5:01 pm - 7:02 pmMCO Orlando-MDW Chicago Midway

3h 01mnonstop

8:07 pm - 11:57 pmMDW Chicago Midway-MCO Orlando

2h 50mnonstop

$254Frontier

Useful Info

Low season	January
High season	July
Cheapest flight	$76

Best time to beat the crowds with an average 2% drop in price.

Most popular time to fly with an average 8% increase in price.

Flight from Valparaiso to Chicago Midway Airport

Verified travelerFlew with Southwest-Sep 2026

Nothing much. just when it's time to check-in, try to check in at the exact 24 time limit window in order to get one of the earlier seats at the front of the plane

CindyFlew with Southwest-Mar 2024

Don’t check a bag. Chicago takes forever to get your baggage.

How does KAYAK find such low prices on flights from Florida to Chicago Midway Airport?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Florida to Chicago Midway Airport.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Florida to Chicago Midway Airport?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Florida is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Florida to Chicago Midway Airport?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Florida with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Florida to Chicago Midway Airport?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Florida up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Chesterton

Porter

Monticello

Saint John

Griffith

More options for your flight to Midway

Add a hotel or car rental

Airports

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

Complete your trip to Midway with a hotel stay or car rental

Car rentals in Chicago

MDW

$76 Find Cheap Flights from Florida to Chicago Midway Airport - Compare and Save

Cheap Flights from Florida to Midway

Recent round-trip flight deals from Florida to Midway

Recent one-way flight deals from Florida to Midway

Recent last minute flight deals from Florida to Midway

Recent direct flight deals from Florida to Midway

Good to know

Low season

High season

Cheapest flight

Flights from Florida to Midway: the best tips from KAYAK users

FAQs for booking Florida to Chicago Midway Airport flights

Traveling to a place near Midway?

More options for your flight to Midway

Complete your trip to Midway with a hotel stay or car rental

Information on your arrival and departure airports

Cabin class types available on flights to Midway

Find direct flights for Midway

Flights from domestic origins to Florida

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight