SRQ - MDW

$139 Find Cheap Flights from Sarasota to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$291
Typical prices: $350-$479
Southwest
Mon 12/3Wed 12/5
SRQ - MDW • Non-stop
Cheapest non-stop
$291
Typical prices: $351-$478
Southwest
Sat 12/8Sun 12/9
SRQ - MDW • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 50m
Direct flights
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Direct flights
+1
When to travel
Cheapest • 16% price drop
Most popular
Good to know
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Good to know
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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

Thu, Dec 3 - Sat, Dec 5
Southwest Logo
12:45 pm - 2:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
3:45 pm - 7:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 35mnonstop
$291Southwest
Tue, Dec 8 - Wed, Dec 9
Southwest Logo
12:45 pm - 2:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
8:05 am - 11:50 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 45mnonstop
$291Southwest
Wed, Dec 2 - Sat, Dec 5
Southwest Logo
12:45 pm - 2:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
3:45 pm - 7:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 35mnonstop
$291Southwest
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
12:45 pm - 2:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
8:05 am - 11:50 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 45mnonstop
$291Southwest
Thu, Dec 3 - Sat, Dec 5
Southwest Logo
12:45 pm - 2:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
7:50 am - 3:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
6h 30m1 stop Nashville Intl
$301Southwest
Mon, Dec 14 - Thu, Dec 17
Southwest Logo
1:55 pm - 7:40 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
6h 45m1 stop Columbus
Southwest Logo
6:50 pm - 10:30 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 40mnonstop
$301Southwest
Mon, Dec 7 - Wed, Dec 9
Southwest Logo
6:45 pm - 10:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
5h 00m1 stop Nashville Intl
Southwest Logo
8:05 am - 11:50 amMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 45mnonstop
$301Southwest
Wed, Dec 2 - Sat, Dec 5
Southwest Logo
12:45 pm - 2:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
7:50 am - 3:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
6h 30m1 stop Nashville Intl
$301Southwest
Tue, Nov 17 - Wed, Dec 2
Delta Logo
5:35 pm - 10:54 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
6h 19m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 1:23 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
6h 23m1 stop Atlanta Hartsfield-Jackson
$311Delta
Thu, Nov 19 - Thu, Nov 26
Delta Logo
6:25 pm - 10:54 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
5h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:13 pm - 11:01 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
5h 48m1 stop Atlanta Hartsfield-Jackson
$311Delta
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 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 typically range from $350 to $479. The lowest price found in the past 5 days was $291, on Southwest.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Sarasota to Chicago Midway Airport. It’s 10% cheaper than the average day, while Sunday is the most expensive, with prices 22% higher.

What’s 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 $331 round-trip.
•November ($883) and January ($754) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 166% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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.

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.

Key details for Sarasota to Chicago Midway Airport flights

Low season

March

Cheapest flight

$139
Beat the crowds with an average 74% drop in travelers.
The most popular month to fly with an average 101% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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 9:00 am
    • Latest: departs at 8:00 pm and lands at 10:50 pm.

    The flight takes about 2h 50m.

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

    A nonstop flight from Sarasota to Chicago Midway Airport takes 2h 50m, 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.

  • 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 $350 to $479, with an average of $396 over the past 12 months. Anything below $350 counts as a good deal.

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

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $399 round-trip, compared to $567 via a layover through Atlanta Hartsfield-Jackson (ATL).

  • 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 Airbus A320-100/200 family is used most often on this route, operated mainly by United Airlines and Allegiant Air. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

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

    Afternoon 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%, evening flights for 0%, and night flights for 0%.

  • 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 $291 to $1,754. That means the highest observed fare was about 6x higher than the lowest one.

  • 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.

  • 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 $149, which is 43% below the typical average for this route.

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

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

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

    Most connecting flights from Sarasota to Chicago Midway Airport pass through Atlanta Hartsfield-Jackson (ATL), which handles 100% of one-stop traffic on this route.

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

    Yes. Flexible dates can save you up to 27% on flights from Sarasota to Chicago Midway Airport. Saturday is the cheapest departure day at $359 round-trip on average, while Sunday is the most expensive at $487, a difference of $128.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Sarasota to Chicago Midway Airport?

    Only Southwest operates flights between Sarasota and Chicago Midway Airport.

  • 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 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 Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • 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.

  • 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 in Economy Class class
    • JetBlue: a cabin bag in Economy Class class

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

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 are flexible, aim for a Saturday departure and avoid flying on Sunday. On this route, Saturday flights average $359, about $128 less than Sunday fares (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 $331 round-trip in that month - typically $552 less than the most expensive month, which is November (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 Chicago Midway Airport

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

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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

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