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.

$68 CHEAP FLIGHTS from Florida to Chicago Midway (MDW)

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Cheap Flights from Florida to Midway

Cheap flights from Florida to Midway with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Fri, Nov 13 - Mon, Nov 16

7:30 am - 9:48 amVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 18mnonstop

1:08 pm - 3:19 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 11mnonstop

$95Allegiant Air

Sat, Nov 7 - Sat, Nov 14

7:15 am - 9:25 amFLL Fort Lauderdale-MDW Chicago Midway

3h 10mnonstop

7:50 am - 2:40 pmMDW Chicago Midway-FLL Fort Lauderdale

5h 50m2 stops Columbus Tampa

$132Southwest

Thu, Nov 5 - Mon, Nov 9

2:22 pm - 11:47 pmFLL Fort Lauderdale-MDW Chicago Midway

10h 25m1 stop Atlanta Hartsfield-Jackson

6:08 am - 3:24 pmMDW Chicago Midway-FLL Fort Lauderdale

8h 16m1 stop Atlanta Hartsfield-Jackson

$133Frontier

Fri, Nov 6 - Mon, Nov 9

6:31 am - 5:47 pmFLL Fort Lauderdale-MDW Chicago Midway

12h 16m1 stop Atlanta Hartsfield-Jackson

6:08 am - 3:24 pmMDW Chicago Midway-FLL Fort Lauderdale

8h 16m1 stop Atlanta Hartsfield-Jackson

$135Frontier

Wed, Nov 25 - Wed, Dec 9

5:30 am - 7:35 amFLL Fort Lauderdale-MDW Chicago Midway

3h 05mnonstop

1:20 pm - 8:40 pmMDW Chicago Midway-FLL Fort Lauderdale

6h 20m2 stops Atlanta Hartsfield-Jackson Tampa

$136Southwest

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

$144Allegiant Air

Tue, Nov 10 - Wed, Nov 11

8:40 am - 5:47 pmFLL Fort Lauderdale-MDW Chicago Midway

10h 07m2 stops Tampa Atlanta Hartsfield-Jackson

6:08 am - 2:39 pmMDW Chicago Midway-FLL Fort Lauderdale

7h 31m1 stop Atlanta Hartsfield-Jackson

$187Multiple Airlines

Fri, Nov 13 - Mon, Nov 16

1:39 pm - 5:47 pmVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

28h 08m2 stops Washington, D.C. Dulles Intl Atlanta Hartsfield-Jackson

1:08 pm - 3:19 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 11mnonstop

$193Multiple Airlines

Wed, Jan 13 - Fri, Jan 29

12:20 pm - 4:25 pmTPA Tampa-MDW Chicago Midway

5h 05m1 stop Atlanta Hartsfield-Jackson

6:00 am - 12:13 pmMDW Chicago Midway-TPA Tampa

5h 13m1 stop Atlanta Hartsfield-Jackson

$225Delta

Tue, Jan 12 - Fri, Jan 29

8:20 am - 12:33 pmTPA Tampa-MDW Chicago Midway

5h 13m1 stop Detroit Metropolitan Wayne County

6:00 am - 12:13 pmMDW Chicago Midway-TPA Tampa

5h 13m1 stop Atlanta Hartsfield-Jackson

$225Delta

Sat, Oct 17 - Tue, Oct 20

6:29 pm - 11:43 pmTPA Tampa-MDW Chicago Midway

6h 14m1 stop Atlanta Hartsfield-Jackson

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

11h 03m1 stop Atlanta Hartsfield-Jackson

$223Frontier

Wed, Oct 14 - Wed, Oct 28

5:57 pm - 11:43 pmTPA Tampa-MDW Chicago Midway

6h 46m1 stop Atlanta Hartsfield-Jackson

6:16 am - 10:35 pmMDW Chicago Midway-TPA Tampa

15h 19m1 stop Atlanta Hartsfield-Jackson

$226Frontier

Wed, Oct 14 - Sat, Oct 24

3:23 pm - 11:43 pmMIA Miami-MDW Chicago Midway

9h 20m1 stop Atlanta Hartsfield-Jackson

6:21 am - 4:51 pmMDW Chicago Midway-MIA Miami

9h 30m1 stop Atlanta Hartsfield-Jackson

$232Frontier

Tue, Oct 13 - Sat, Oct 31

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

3h 10mnonstop

5:25 am - 12:45 pmMDW Chicago Midway-FLL Fort Lauderdale

6h 20m1 stop Tampa

$279Southwest

Wed, Oct 14 - Wed, Oct 28

6:00 pm - 7:40 pmTPA Tampa-MDW Chicago Midway

2h 40mnonstop

1:00 pm - 6:20 pmMDW Chicago Midway-TPA Tampa

4h 20m1 stop Pittsburgh

$292Southwest

Wed, Oct 14 - Wed, Oct 28

5:57 pm - 11:43 pmTPA Tampa-MDW Chicago Midway

6h 46m1 stop Atlanta Hartsfield-Jackson

6:16 am - 7:10 amMDW Chicago Midway-TPA Tampa

23h 54m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

$293Multiple Airlines

Wed, Oct 14 - Wed, Oct 28

5:57 pm - 11:43 pmTPA Tampa-MDW Chicago Midway

6h 46m1 stop Atlanta Hartsfield-Jackson

6:16 am - 7:10 amMDW Chicago Midway-TPA Tampa

23h 54m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

$294Multiple Airlines

Tue, Oct 13 - Sat, Oct 31

7:00 am - 2:40 pmFLL Fort Lauderdale-MDW Chicago Midway

8h 40m2 stops Orlando Miami

6:05 am - 4:45 pmMDW Chicago Midway-FLL Fort Lauderdale

9h 40m2 stops Lambert-St Louis Nashville Intl

$299Southwest

Sat, Oct 17 - Mon, Oct 26

5:00 pm - 10:33 pmFLL Fort Lauderdale-MDW Chicago Midway

6h 33m1 stop Atlanta Hartsfield-Jackson

6:04 am - 12:22 pmMDW Chicago Midway-FLL Fort Lauderdale

5h 18m1 stop Atlanta Hartsfield-Jackson

$329Delta

Fri, Oct 16 - Fri, Oct 23

11:43 am - 6:00 pmFLL Fort Lauderdale-MDW Chicago Midway

7h 17m1 stop Detroit Metropolitan Wayne County

6:04 am - 2:33 pmMDW Chicago Midway-FLL Fort Lauderdale

7h 29m1 stop Atlanta Hartsfield-Jackson

$350Delta

Fri, Nov 13 - Mon, Nov 16

7:30 am - 9:48 amVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 18mnonstop

1:08 pm - 3:19 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 11mnonstop

$95Allegiant 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

$144Allegiant Air

Fri, Feb 26 - Mon, Mar 1

8:35 pm - 10:50 pmFLL Fort Lauderdale-MDW Chicago Midway

3h 15mnonstop

6:10 am - 10:10 amMDW Chicago Midway-FLL Fort Lauderdale

3h 00mnonstop

$146Southwest

Fri, Oct 30 - Mon, Nov 2

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

3h 10mnonstop

7:30 pm - 11:25 pmMDW Chicago Midway-FLL Fort Lauderdale

2h 55mnonstop

$146Southwest

Sat, Oct 31 - Mon, Nov 2

7:20 am - 9:25 amFLL Fort Lauderdale-MDW Chicago Midway

3h 05mnonstop

7:30 pm - 11:25 pmMDW Chicago Midway-FLL Fort Lauderdale

2h 55mnonstop

$152Southwest

Mon, Nov 2 - Mon, Nov 9

3:36 pm - 5:54 pmVPS Valparaiso Destin-Ft Walton Beach-MDW Chicago Midway

2h 18mnonstop

1:08 pm - 3:19 pmMDW Chicago Midway-VPS Valparaiso Destin-Ft Walton Beach

2h 11mnonstop

$155Allegiant 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

$157Allegiant Air

Fri, Dec 18 - Mon, Dec 21

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

3h 01mnonstop

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

2h 50mnonstop

$199Frontier

Thu, Dec 10 - Mon, Dec 14

6:42 pm - 8:42 pmMCO Orlando-MDW Chicago Midway

3h 00mnonstop

9:37 pm - 1:25 amMDW Chicago Midway-MCO Orlando

2h 48mnonstop

$201Frontier

Thu, Dec 24 - Tue, Dec 29

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

3h 01mnonstop

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

2h 50mnonstop

$202Frontier

Low season	January
High season	July
Cheapest flight	$68

Best time to beat the crowds with an average 4% drop in price.

Most popular time to fly with an average 5% 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

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

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MDW

$68 Find Cheap Flights from Florida to Chicago Midway Airport - Compare and Save

Cheap Flights from Florida to Midway

Cheap flights from Florida to Midway with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

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

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