BOS - MDW

$111 Find Cheap Flights from Boston to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$218
Typical prices: $205-$351
Frontier
Sat 11/17Wed 11/21
BOS - MDW • 1 stop
Cheapest non-stop
$247
Typical prices: $208-$351
Southwest
Mon 12/3Fri 12/7
BOS - 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 book
6 weeks
in advance
Our data shows that travelers who book at least 6 weeks in advance save around 28% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 38% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $157 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 4h 15m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
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Flight Deals

Cheap Flights from Boston to Midway (BOS-MDW)

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

Recent round-trip flight deals from Boston to Midway

Tue, Nov 17 - Sat, Nov 21
Frontier Logo
12:15 pm - 11:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
12h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:42 pm - 10:11 amMDW  Chicago Midway-BOS Boston Logan Intl
12h 29m1 stop Orlando
$218Frontier
Tue, Mar 2 - Wed, Mar 3
Frontier Logo
10:24 am - 7:42 pmBOS  Boston Logan Intl-MDW Chicago Midway
10h 18m1 stop Orlando
Frontier Logo
8:47 pm - 9:29 amMDW  Chicago Midway-BOS Boston Logan Intl
11h 42m1 stop Orlando
$220Frontier
Sat, Nov 21 - Tue, Nov 24
Frontier Logo
8:26 am - 1:45 pmBOS  Boston Logan Intl-MDW Chicago Midway
6h 19m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:42 pm - 10:11 amMDW  Chicago Midway-BOS Boston Logan Intl
12h 29m1 stop Orlando
$220Frontier
Sat, Nov 14 - Sat, Nov 21
Frontier Logo
11:27 am - 5:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 20m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:42 pm - 10:11 amMDW  Chicago Midway-BOS Boston Logan Intl
12h 29m1 stop Orlando
$220Frontier
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
5:55 pm - 7:40 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
8:30 am - 12:00 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 30mnonstop
$247Southwest
Mon, Feb 1 - Wed, Feb 10
Southwest Logo
12:50 pm - 2:35 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
1:25 pm - 4:40 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
$247Southwest
Tue, Dec 8 - Thu, Dec 10
Southwest Logo
5:55 pm - 7:40 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
1:15 pm - 4:20 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 05mnonstop
$247Southwest
Thu, Dec 10 - Sat, Dec 12
Delta Logo
9:05 am - 1:01 pmBOS  Boston Logan Intl-MDW Chicago Midway
4h 56m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 12:33 pmMDW  Chicago Midway-BOS Boston Logan Intl
5h 33m1 stop Atlanta Hartsfield-Jackson
$325Delta
Thu, Dec 10 - Sat, Dec 12
Delta Logo
5:27 am - 9:37 amBOS  Boston Logan Intl-MDW Chicago Midway
5h 10m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 pm - 11:58 pmMDW  Chicago Midway-BOS Boston Logan Intl
4h 17m1 stop Detroit Metropolitan Wayne County
$325Delta
Wed, Jan 13 - Sat, Jan 16
Delta Logo
5:30 am - 9:16 amBOS  Boston Logan Intl-MDW Chicago Midway
4h 46m1 stop Detroit Metropolitan Wayne County
Delta Logo
10:47 am - 6:58 pmMDW  Chicago Midway-BOS Boston Logan Intl
7h 11m1 stop Atlanta Hartsfield-Jackson
$325Delta
Booking Insights

Price, demand and travel trends for Boston 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 Boston to Chicago Midway Airport?

Round-trip flights from Boston to Chicago Midway Airport typically range from $205 to $351. The lowest price found in the past 5 days was $218, on Frontier.

What's the cheapest day of the week to fly from Boston 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 Boston to Chicago Midway Airport. It’s 18% cheaper than the average day, while Friday is the most expensive, with prices 7% higher.

What’s the cheapest month to fly from Boston to Chicago Midway Airport?

•January is the cheapest month to fly from Boston to Chicago Midway Airport at $167 round-trip.
•November ($343) and October ($312) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 105% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Boston to Chicago Midway Airport the cheapest?

Flights from Boston to Chicago Midway Airport are cheapest 6 weeks before departure. Booking in this window typically costs about 28% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice

Expert advice for your flight from Boston 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
Blane Bachelor

Blane Bachelor

Expert on BOS

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more

Key details for Boston to Chicago Midway Airport flights

Low season

February

Cheapest flight

$118
Beat the crowds with an average 44% drop in travelers.
The most popular month to fly with an average 33% increase in travelers.
One-way flight from Boston to Chicago Midway Airport

When to book flights from Boston to Midway

Are your dates flexible? Find out the best times to travel from Boston 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 Boston 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 Boston to Chicago Midway Airport?

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

    • Earliest: departs at 5:50 am and lands at 8:37 am
    • Latest: departs at 10:25 pm and lands at 1:12 am.

    The flight takes about 2h 47m.

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

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

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

    A nonstop flight from Boston to Chicago Midway Airport takes 2h 47m, covering 857 miles.

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

    Round-trip flights from Boston to Chicago Midway Airport range from $205 to $351, with an average of $269 over the past 12 months. Anything below $205 counts as a good deal.

  • How expensive are last-minute Boston to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 18% above the $269 route average. Book 6 weeks before departure for the lowest fares.

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $157 round-trip via Orlando (MCO), compared to $271 for nonstop.

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

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Boeing 737-800 variants.

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

    Morning is the busiest departure period on Boston to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

  • Have flight prices from Boston 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 $218 to $1,110. That means the highest observed fare was about 5x higher than the lowest one.

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

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

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

    One-way fares from Boston to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $134, which is 21% 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 starting from around $32 for economy cars. Top options include:

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

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

    Flights from Boston to Chicago Midway Airport usually depart from Boston Logan Intl (BOS) and arrive at Chicago Midway (MDW).

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

    One-stop flights from Boston to Chicago Midway Airport most commonly connect through:

    • Detroit Metropolitan Wayne County (DTW) - 38% of one-stop connections
    • Lambert-St Louis (STL) - 25% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 17% of one-stop connections
    • Orlando (MCO) - 17% of one-stop connections

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

    Yes. Flexible dates can save you up to 23% on flights from Boston to Chicago Midway Airport. Saturday is the cheapest departure day at $223 round-trip on average, while Friday is the most expensive at $289, a difference of $66.

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

  • What airlines fly from Boston to Chicago Midway Airport?

    Only Southwest operates flights between Boston and Chicago Midway Airport.

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

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 15m, compared with 5h 27m via Baltimore/Washington (BWI) and 5h 55m via Lambert-St Louis (STL).

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

    Chicago Midway Airport is 1 hour behind Boston (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 Boston to Chicago Midway Airport flights?

    Among airlines operating Boston 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 Boston 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 always check the fare details before booking.

Your guide to booking Boston 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 Friday. On this route, Saturday flights average $223, about $66 less than Friday fares (23% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 6 weeks before you fly. On this route, that window historically saves about 28% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Boston to Chicago Midway Airport trip for January. Fares historically average $167 round-trip in that month - typically $176 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Orlando Airport (MCO) can be cheaper than flying direct. The cheapest layover option averages $157 round-trip on this route - about $114 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 Boston to Chicago Midway Airport?

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

Direct departures

Boston Logan Intl to Chicago Midway

Monday

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Southwest

Tuesday

Southwest

Southwest

Wednesday

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Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Boston Logan Intl

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

More options for your flight from Boston to Midway

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

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