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Boston Logan International Airport to Chicago Midway International Airport flight

Explore the cheapest one-way and round-trip flights from Boston Logan International Airport to Chicago Midway International Airport over the next 90 days, with one-way fares from US$ 93 and round-trip from US$ 180. Based on Trip.com's latest 7-day flight data.

    • Cheapest
      BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Sat, Oct 31 | Frontier Airlines
      US$ 93 US$ 137
      32% off
      32% off
      US$ 137 US$ 93
    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Mon, Dec 7 | Delta Air Lines
      US$ 104 US$ 137
      24% off
      24% off
      US$ 137 US$ 104
    • BOS 15:15
      8h 18m
      1 stop
      MDW 22:33
      Boston - Chicago | Sat, Oct 31 | Delta Air Lines
      US$ 104 US$ 137
      24% off
      24% off
      US$ 137 US$ 104
    • BOS 17:50
      2h 45m
      Direct
      MDW 19:35
      Boston - Chicago | Tue, Nov 17 | Hahn Air
      US$ 107
      22% off
      US$ 137 US$ 107
    • BOS 06:20
      6h 44m
      1 stop
      MDW 12:04
      Boston - Chicago | Thu, Dec 10 | Delta Air Lines
      US$ 109
      20% off
      US$ 137 US$ 109
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Thu, Oct 29 | Normal Airline
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    • BOS 11:06
      9h 41m
      1 stop
      MDW 19:47
      Boston - Chicago | Sun, Nov 22 | Frontier Airlines
      ORD 05:40
      27h 31m
      1 stop
      BOS 10:11
      Chicago - Boston | Wed, Nov 25 | Frontier Airlines
      US$ 180 US$ 240
      25% off
      25% off
      US$ 240 US$ 180
    • BOS 12:15
      6h 32m
      1 stop
      MDW 17:47
      Boston - Chicago | Thu, Nov 19 | Frontier Airlines
      MDW 18:42
      11h 59m
      1 stop
      BOS 07:41
      Chicago - Boston | Sat, Nov 21 | Frontier Airlines
      US$ 181 US$ 240
      25% off
      25% off
      US$ 240 US$ 181
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Sat, Nov 21 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Wed, Nov 25 | Frontier Airlines
      US$ 182 US$ 240
      24% off
      24% off
      US$ 240 US$ 182
    • BOS 12:39
      12h 8m
      1 stop
      MDW 23:47
      Boston - Chicago | Fri, Nov 20 | Frontier Airlines
      MDW 20:42
      12h 29m
      1 stop
      BOS 10:11
      Chicago - Boston | Thu, Nov 26 | Frontier Airlines
      US$ 182
      24% off
      US$ 240 US$ 182
    • BOS 10:25
      10h 5m
      1 stop
      MDW 19:30
      Boston - Chicago | Sat, Dec 19 | Frontier Airlines
      MDW 20:35
      11h 55m
      1 stop
      BOS 09:30
      Chicago - Boston | Mon, Dec 21 | Frontier Airlines
      US$ 184
      23% off
      US$ 240 US$ 184
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Thu, Oct 29 | Normal Airline
      CHI 15:00
      6h
      Direct
      BOS 16:00
      Chicago - Boston | Sat, Oct 31 | Normal Airline
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    • Cheapest nonstop
      BOS 17:50
      2h 45m
      Direct
      MDW 19:35
      Boston - Chicago | Tue, Nov 17 | Hahn Air
      US$ 107 US$ 137
      22% off
      22% off
      US$ 137 US$ 107
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Thu, Oct 29 | Normal Airline
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    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Fri, Dec 25 | Delta Air Lines
      US$ 154 US$ 365
      57% off
      57% off
      US$ 365 US$ 154
    • BOS 05:30
      4h 20m
      1 stop
      MDW 08:50
      Boston - Chicago | Sat, Dec 26 | Delta Air Lines
      US$ 166 US$ 365
      55% off
      55% off
      US$ 365 US$ 166
    • BOS 09:05
      4h 56m
      1 stop
      MDW 13:01
      Boston - Chicago | Sun, Dec 6 | Delta Air Lines
      US$ 176 US$ 365
      52% off
      52% off
      US$ 365 US$ 176
    • BOS 05:30
      5h 16m
      1 stop
      MDW 09:46
      Boston - Chicago | Sat, Nov 28 | Delta Air Lines
      US$ 184
      50% off
      US$ 365 US$ 184
    • BOS 13:04
      5h 40m
      1 stop
      MDW 17:44
      Boston - Chicago | Thu, Dec 24 | Delta Air Lines
      US$ 241
      34% off
      US$ 365 US$ 241
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Thu, Oct 29 | Normal Airline
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    • BOS 17:50
      2h 45m
      Direct
      MDW 19:35
      Boston - Chicago | Tue, Nov 17 | Hahn Air
      US$ 107 US$ 137
      22% off
      22% off
      US$ 137 US$ 107
    • BOS 17:45
      6h 9m
      1 stop
      MDW 22:54
      Boston - Chicago | Mon, Dec 7 | Delta Air Lines
      US$ 104 US$ 137
      24% off
      24% off
      US$ 137 US$ 104
    • BOS 06:20
      6h 44m
      1 stop
      MDW 12:04
      Boston - Chicago | Thu, Dec 10 | Delta Air Lines
      US$ 109 US$ 137
      20% off
      20% off
      US$ 137 US$ 109
    • BOS 11:27
      7h 20m
      1 stop
      MDW 17:47
      Boston - Chicago | Sat, Oct 31 | Frontier Airlines
      US$ 93
      32% off
      US$ 137 US$ 93
    • BOS 15:15
      8h 18m
      1 stop
      MDW 22:33
      Boston - Chicago | Sat, Oct 31 | Delta Air Lines
      US$ 104
      24% off
      US$ 137 US$ 104
    • BOS 13:00
      17h 25m
      1 stop
      CHI 14:00
      Boston - Chicago | Thu, Oct 29 | Normal Airline
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Displayed flight fares from Boston to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Which airline offers the cheapest flights from Boston Logan International Airport to Chicago Midway International Airport?

The cheapest airline flying from Boston Logan International Airport to Chicago Midway International Airport is Frontier Airlines (from US$ 99) among 6 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From US$ 99
Delta Air Lines
From US$ 104
Hahn Air
From US$ 154
Allegiant Air
From US$ 294
Jetblue Airways
From US$ 363
Alaska Airlines
From US$ 393

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What is the flight schedule from Boston Logan International Airport to Chicago Midway International Airport?

Check the schedule for flights from Boston to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL1748

    Boston Logan International Airport

    09:00

    BOS

    2h 26m

    Direct

    11:26

    DTW

    S M T W T F S
    Search

  2. DL4688

    Detroit Metropolitan Wayne County Airport

    12:28

    DTW

    1h 19m

    Direct

    12:47

    MDW

    S M T W T F S

  3. DL2464

    Boston Logan International Airport

    18:55

    BOS

    3h 5m

    Direct

    22:00

    ATL

    - - T - - - -
    Search

  4. DL1076

    Hartsfield–Jackson Atlanta International Airport

    22:59

    ATL

    1h 56m

    Direct

    23:55

    MDW

    S M T W T F S

  5. F93511

    Boston Logan International Airport

    12:39

    BOS

    3h 20m

    Direct

    15:59

    ATL

    S M T W T F S
    Search

  6. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    S M T W T F S

  7. DL2222

    Boston Logan International Airport

    12:55

    BOS

    2h 18m

    Direct

    15:13

    DTW

    S M T W T F S
    Search

  8. DL4677

    Detroit Metropolitan Wayne County Airport

    17:40

    DTW

    1h 20m

    Direct

    18:00

    MDW

    S M T W T F S

  9. DL695

    Boston Logan International Airport

    06:45

    BOS

    3h 13m

    Direct

    09:58

    ATL

    S M T W T F S
    Search

  10. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00

    ATL

    1h 56m

    Direct

    11:56

    MDW

    - - T W T - -

  11. DL1710

    Boston Logan International Airport

    15:10

    BOS

    3h 1m

    Direct

    18:11

    ATL

    S M T W T F S
    Search

  12. DL1076

    Hartsfield–Jackson Atlanta International Airport

    22:59

    ATL

    1h 56m

    Direct

    23:55

    MDW

    S M T W T F S

  13. DL2330

    Boston Logan International Airport

    16:20

    BOS

    3h 3m

    Direct

    19:23

    ATL

    S M T W T F S
    Search

  14. DL1076

    Hartsfield–Jackson Atlanta International Airport

    22:59

    ATL

    1h 56m

    Direct

    23:55

    MDW

    S M T W T F S

  15. F93511

    Boston Logan International Airport

    12:39

    BOS

    3h 20m

    Direct

    15:59

    ATL

    S M T W T F S
    Search

  16. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:45

    ATL

    1h 58m

    Direct

    23:43

    MDW

    S M T W T - S
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About Boston Logan International Airport and Chicago Midway International Airport

Learn about Boston Logan International Airport (BOS) and Chicago Midway International Airport (MDW) — including location, terminals, transportation, and travel tips.

Flight distance 1,380.83km
Cheapest one-way ticket price US$ 93
Cheapest return ticket price US$ 180

FAQs for Boston Logan International Airport to Chicago Midway International Airport Flights

  • How long is the flight from Boston Logan International Airport to Chicago Midway International Airport?

    Boston Logan International Airport to Chicago Midway International Airport takes about 2 hours 6 minutes on average. Actual flight time may vary depending on route, weather and air traffic.
  • There are around 4 daily flights from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW).
  • The earliest flight from Boston Logan International Airport to Chicago Midway International Airport departs at 05:50, and the last departs at 22:50, with about 12 flights per day. Flight times may change, so please check the latest departure and arrival times before you travel.
  • The route from Boston Logan International Airport (BOS) to Chicago Midway International Airport (MDW) is quite popular. Without considering departure times or holidays, tickets cost around US$ 257 in November, the most expensive month to book this route.
  • The earliest flight departs from Boston Logan International Airport (BOS) at 05:20 and arrives in Chicago Midway International Airport (MDW) at 06:55.
  • The latest flight departs from Boston Logan International Airport (BOS) at 18:35 and arrives in Chicago Midway International Airport (MDW) at 20:20.
    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.
  • One-way flights from Boston Logan International Airport to Chicago Midway International Airport currently start from US$ 93, and round-trip fares start from US$ 180. The current lowest fare is a Frontier Airlines flight departing on Sat, Oct 31; prices may vary depending on availability.
  • Based on Trip.com flight data for departures within the next 30 days with at most one stop, the average one-way price from Boston Logan International Airport to Chicago Midway International Airport is US$ 159. Prices may vary depending on the departure date, airline, and availability.
  • Enter Boston Logan International Airport and Chicago Midway International Airport, select your departure date and number of passengers, then compare flights by price, flight duration, and baggage allowance. Once you've chosen a fare, review the change and refund rules, fill in passenger details, and pay to receive your booking confirmation.

Most popular destination

Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, regulatory fees, etc) with all fees confirmed before payment. Fees for baggage, meals, Wi-Fi, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.