SRQ - MDW

$109 Find Cheap Flights from Sarasota to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$282
Typical prices: $351-$507
Allegiant Air
Thu 11/15Tue 11/20
SRQ - MDW • 1 stop
Cheapest non-stop
$318
Typical prices: $351-$507
Southwest
Mon 10/22Fri 10/26
SRQ - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 47m
Direct flights
+1
Direct flights
+1
When to travel
August
Cheapest • 15% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Baltimore/Washington (BWI)
Cheapest • Avg $292 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 5h 05m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Sarasota to Midway (SRQ-MDW)

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

Recent round-trip flight deals from Sarasota to Midway

Sun, Nov 15 - Fri, Nov 20
Allegiant Air Logo
12:35 pm - 3:41 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
28h 06m1 stop Knoxville McGhee Tyson
Allegiant Air Logo
2:30 pm - 11:34 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
8h 04m1 stop Knoxville McGhee Tyson
$282Allegiant Air
Tue, Oct 27 - Fri, Oct 30
Southwest Logo
6:40 pm - 10:15 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
4h 35m1 stop Nashville Intl
Southwest Logo
6:40 pm - 10:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
$313Southwest
Thu, Oct 22 - Mon, Oct 26
Southwest Logo
5:10 pm - 6:55 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
6:40 pm - 10:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
$318Southwest
Tue, Oct 27 - Fri, Oct 30
Southwest Logo
7:15 am - 3:30 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
9h 15m2 stops Orlando Lambert-St Louis
Southwest Logo
6:40 pm - 10:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
$318Southwest
Thu, Oct 15 - Mon, Oct 19
Southwest Logo
6:10 am - 7:55 amSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
6:40 pm - 10:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
$318Southwest
Thu, Oct 15 - Mon, Oct 19
Southwest Logo
6:20 pm - 12:25 amSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
7h 05m1 stop Orlando
Southwest Logo
6:40 pm - 10:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
$328Southwest
Thu, Oct 22 - Mon, Oct 26
Southwest Logo
1:55 pm - 7:15 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
6h 20m1 stop Lambert-St Louis
Southwest Logo
8:10 am - 11:50 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
$328Southwest
Tue, Oct 27 - Fri, Oct 30
Southwest Logo
7:15 am - 12:25 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
6h 10m2 stops Orlando Atlanta Hartsfield-Jackson
Southwest Logo
7:05 am - 1:10 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
5h 05m1 stop Nashville Intl
$328Southwest
Tue, Oct 27 - Fri, Oct 30
Southwest Logo
7:15 am - 2:25 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
8h 10m2 stops Orlando Atlanta Hartsfield-Jackson
Southwest Logo
2:50 pm - 11:00 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
7h 10m2 stops Detroit Metropolitan Wayne County Baltimore/Washington
$333Southwest
Wed, Oct 14 - Tue, Oct 20
Delta Logo
7:00 am - 11:54 amSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
5h 54m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:59 am - 4:28 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
4h 29m1 stop Atlanta Hartsfield-Jackson
$359Delta
Booking Insights

Price, demand and travel trends for Sarasota to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Sarasota to Chicago Midway Airport with more confidence.

How much is a round-trip flight from Sarasota to Chicago Midway Airport?

Round-trip flights from Sarasota to Chicago Midway Airport start at $282. Prices are below average for this route right now, with typical round-trip fares ranging from $351 to $507. The lowest price found in the past 5 days was $282 on Allegiant Air.

What's the cheapest day of the week to fly from Sarasota to Chicago Midway Airport?

Saturday is the cheapest day of the week to fly from Sarasota to Chicago Midway Airport, it is 12% cheaper than the average day. Sunday is the most expensive day with flight prices 20% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Sarasota to Chicago Midway Airport?

  • August is the cheapest month to fly from Sarasota to Chicago Midway Airport at $345 round-trip.
  • January ($754) and March ($640) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 118% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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Expert advice

Expert advice for your flight from Sarasota to Midway

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on SRQ

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Key details for Sarasota to Chicago Midway Airport flights

Low season

March

Cheapest flight

$109
Best time to beat the crowds but there is an average 58% increase in price.
Most popular time to fly with an average 2% increase in price.
Flight from Sarasota to Chicago Midway Airport

When to book flights from Sarasota to Midway

Are your dates flexible? Find out the best times to travel from Sarasota to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Sarasota to Chicago Midway Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines offer extra legroom and free seat selection on Sarasota to Chicago Midway Airport flights?

    Among airlines operating Sarasota to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Sarasota to Chicago Midway Airport?

    Only Southwest operates flights between Sarasota and Chicago Midway Airport.

  • Which airports can I use when flying from Sarasota to Chicago Midway Airport?

    Flights from Sarasota to Chicago Midway Airport usually depart from Sarasota Bradenton Intl (SRQ) and arrive at Chicago Midway (MDW).

  • Which airlines include bags at no extra cost on Sarasota to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Sarasota to Chicago Midway Airport?

    Only Economy Class is available on flights from Sarasota to Chicago Midway Airport.

  • How much can I save by taking a layover when flying from Sarasota to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $292 round-trip via Baltimore/Washington (BWI), compared to $410 for nonstop.

  • What is the standard checked-bag allowance on flights from Sarasota to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Sarasota to Chicago Midway Airport?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest. Other aircraft seen on the route include Airbus A320-100/200 variants.

  • Which airports do connecting flights from Sarasota to Chicago Midway Airport pass through?

    Connecting flights from Sarasota to Chicago Midway Airport most commonly pass through:

    • Atlanta Hartsfield-Jackson (ATL) - 89% of one-stop connections
    • Baltimore/Washington (BWI) - 11% of one-stop connections
    Together, these airports account for 100% of one-stop bookings on this route.

  • Can I save money by using flexible dates for flights from Sarasota to Chicago Midway Airport?

    On the Sarasota to Chicago Midway Airport route, being flexible with your departure day can save you up to 27%. Saturday is the cheapest day at $359 round-trip on average, while Sunday is the most expensive at $487: a $128 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • How are flight departures from Sarasota to Chicago Midway Airport spread across the day?

    Evening is the busiest departure period on Sarasota to Chicago Midway Airport flights, with 100% of flights leaving in that window. Morning departures account for 0%, afternoon flights for 0%, and night flights for 0%.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • What are the earliest and latest flights from Sarasota to Chicago Midway Airport?

    These are the earliest and latest flight times available from Sarasota to Chicago Midway Airport:

    • Earliest: departs at 6:10 am and lands at 8:57 am
    • Latest: departs at 8:00 pm and lands at 10:47 pm.

    The flight takes about 2h 47m.

  • How long is a flight from Sarasota to Chicago Midway Airport?

    A nonstop flight from Sarasota to Chicago Midway Airport takes 2h 47m, covering 1,036 miles.

  • Do I need a passport to fly from Sarasota to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Sarasota to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $247 to $1,940. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Sarasota to Chicago Midway Airport looking right now?

    One-way fares from Sarasota to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $128, which is 50% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Sarasota to Chicago Midway Airport?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 5h 05m, compared with 5h 14m via Baltimore/Washington (BWI).

  • What is the time difference between Sarasota and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Sarasota (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • How much should I expect to pay for a Sarasota to Chicago Midway Airport flight?

    Round-trip flights from Sarasota to Chicago Midway Airport range from $351 to $507, with an average of $405 over the past 12 months. Anything below $351 counts as a good deal.

  • Which airlines offer Wi-Fi on Sarasota to Chicago Midway Airport flights?

    JetBlue is the only airline on the Sarasota to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

Your guide to booking Sarasota to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Saturday departure instead of Sunday. On this route, Saturday flights average $359 - about $128 less than Sunday (26% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Sarasota to Chicago Midway Airport trip for August. Fares historically average $345 round-trip in that month - typically $409 less than the most expensive month, which is January (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Baltimore/Washington Airport (BWI) can be cheaper than flying direct. The cheapest layover option averages $292 round-trip on this route - about $118 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

Prefer to fly direct from Sarasota to Chicago Midway Airport?

 
Find which airlines fly direct from Sarasota Bradenton Intl Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Sarasota Bradenton Intl to Chicago Midway

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to Sarasota Bradenton Intl

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

More options for your flight from Sarasota to Midway

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