$49 Cheap flights from Northwest Florida Regional to Midway Intl. (VPS to MDW)

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Find The Best Dates To Fly from Northwest Florida Regional to Midway Intl.

Compare Flight Prices from Fort Walton Beach to Chicago

Affordable Airfare Tickets from VPS to MDW Airport

The cheapest flights to Midway Intl. found within the past 7 days were $88 round trip and $49 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Oct 16 - Fri, Oct 23
VPS
Fort Walton Beach
MDW
Chicago
$88 Roundtrip, found 2 days ago
$88
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Fri, Oct 16 from Fort Walton Beach to Chicago, returning Fri, Oct 23, priced at $88 found 2 days ago
Fri, Nov 6 - Fri, Nov 13
VPS
Fort Walton Beach
MDW
Chicago
$92 Roundtrip, found 4 hours ago
$92
Roundtrip
found 4 hours ago
Select Allegiant Air flight, departing Fri, Nov 6 from Fort Walton Beach to Chicago, returning Fri, Nov 13, priced at $92 found 4 hours ago
Fri, Nov 6 - Mon, Nov 9
VPS
Fort Walton Beach
MDW
Chicago
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Nov 6 from Fort Walton Beach to Chicago, returning Mon, Nov 9, priced at $97 found 1 day ago
Fri, Oct 16 - Fri, Oct 23
VPS
Fort Walton Beach
MDW
Chicago
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Oct 16 from Fort Walton Beach to Chicago, returning Fri, Oct 23, priced at $99 found 1 day ago
Fri, Oct 30 - Fri, Nov 6
VPS
Fort Walton Beach
MDW
Chicago
$102 Roundtrip, found 4 days ago
$102
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Fri, Oct 30 from Fort Walton Beach to Chicago, returning Fri, Nov 6, priced at $102 found 4 days ago
Fri, Oct 9 - Fri, Oct 23
VPS
Fort Walton Beach
MDW
Chicago
$105 Roundtrip, found 1 day ago
$105
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Oct 9 from Fort Walton Beach to Chicago, returning Fri, Oct 23, priced at $105 found 1 day ago
Fri, Oct 16 - Mon, Oct 19
VPS
Fort Walton Beach
MDW
Chicago
$107 Roundtrip, found 6 days ago
$107
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Oct 16 from Fort Walton Beach to Chicago, returning Mon, Oct 19, priced at $107 found 6 days ago
Fri, Oct 2 - Mon, Oct 5
VPS
Fort Walton Beach
MDW
Chicago
$109 Roundtrip, found 1 hour ago
$109
Roundtrip
found 1 hour ago
Select Allegiant Air flight, departing Fri, Oct 2 from Fort Walton Beach to Chicago, returning Mon, Oct 5, priced at $109 found 1 hour ago
Mon, Aug 10 - Mon, Aug 17
VPS
Fort Walton Beach
MDW
Chicago
$112 Roundtrip, found 4 days ago
$112
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Mon, Aug 10 from Fort Walton Beach to Chicago, returning Mon, Aug 17, priced at $112 found 4 days ago
Fri, Oct 2 - Mon, Oct 5
VPS
Fort Walton Beach
MDW
Chicago
$116 Roundtrip, found 9 hours ago
$116
Roundtrip
found 9 hours ago
Select Allegiant Air flight, departing Fri, Oct 2 from Fort Walton Beach to Chicago, returning Mon, Oct 5, priced at $116 found 9 hours ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $1,396, price is now $1,032 per person
$1,032
per person
Sep 3 - Sep 7
found 1 hour ago
Roundtrip flight included
Fort Walton Beach (VPS) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,815, price is now $1,324 per person
$1,324
per person
Sep 3 - Sep 7
found 1 hour ago
Roundtrip flight included
Fort Walton Beach (VPS) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $1,598, price is now $1,194 per person
$1,194
per person
Sep 3 - Sep 7
found 1 hour ago
Roundtrip flight included
Fort Walton Beach (VPS) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $1,459, price is now $1,137 per person
$1,137
per person
Sep 3 - Sep 7
found 1 hour ago
Roundtrip flight included
Fort Walton Beach (VPS) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was $1,996, price is now $1,556 per person
$1,556
per person
Sep 3 - Sep 7
found 1 hour ago
Roundtrip flight included
Fort Walton Beach (VPS) to Chicago (ORD)
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Frequently asked questions

Can I catch a flight from Destin–Fort Walton Beach Airport to Midway Intl. Airport (MDW) right now?
It's wise to find out about any travel advice reports and quarantine requirements in place in your destination. Ensure you visit the Covid-19 Travel Advisor for up-to-date information on catching a flight to Chicago Airport from VPS.
Are there direct flights from VPS to Midway Intl. Airport (MDW)?
Multiple airlines advertise flights straight from VPS to MDW. Among these are Southwest Airlines and Allegiant Air — start with these if you need to arrive at your destination sooner rather than later.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to Midway Intl. Airport (MDW), please visit our Customer Service Portal.
How long is the flight from Northwest Florida Regional Airport (VPS) to Midway Intl. Airport (MDW)?
Step off the plane feeling relaxed and rested by having a snooze and a snack during your flight to Midway Airport. With a travel time of around 3 hours and 20 minutes from VPS, you'll have plenty of time to enjoy both.
What is the flight distance from Northwest Florida Regional Airport (VPS) to MDW?
There's a flight distance of 780 mi between VPS and Chicago Airport. Take advantage of your short plane ride to write down all the places you plan to visit and how you're going to get there. A comprehensive itinerary is key to having an unforgettable vacation.
What airlines fly from Destin–Fort Walton Beach Airport to MDW?
There are a number of airlines advertising direct flights between Valparaiso and Chicago. Southwest Airlines (WN) is one of the most popular. This carrier operates 17 flights every month. It's a good idea to also look into the deals available through Allegiant Air (G4). Another well-known airline, it operates 8 flights every month on the Valparaiso to Chicago route. Compare the two to pick up the best fare.
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you're flying with Southwest Airlines, Delta or Volaris you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Flight information from Fort Walton Beach to Chicago

 

Traveling From
Northwest Florida Regional
Traveling To
Midway Intl.
Shortest Flight Time
 hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price
$88

Route Info

Flight path for flights from Northwest Florida Regional Airport to Chicago Midway International Airport.


Origin:
VPS - Northwest Florida Regional Airport
Destination:
MDW - Chicago Midway International Airport
Distance:
845.00 miles


Discover our best flights from Fort Walton Beach VPS to Chicago MDW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Fort Walton Beach VPS to Chicago MDW at the right price  

Airfares to Chicago MDW from Fort Walton Beach VPS currently cost between $88 and $116. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Fort Walton Beach VPS to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Fort Walton Beach VPS to Chicago MDW on Travelocity starting at $49. Prices and availability subject to change. Additional terms may apply. 

 

Get to Chicago MDW from Fort Walton Beach VPS quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from VPS to take around hour(s) min(s).  

 

Find our cheapest airfares for flights from Fort Walton Beach VPS to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from VPS. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Fort Walton Beach VPS to Chicago MDW today 

If you’re flexible about when you travel, October is usually the cheapest month to fly from Fort Walton Beach VPS to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Chicago MDW from Fort Walton Beach VPS 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from VPS have this option.  

 

Travel with confidence when you book flights to Chicago MDW from Fort Walton Beach VPS with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

Explore More Ways to Travel with Travelocity

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.