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Chicago Midway International Airport to Boston Logan International Airport flight

Find the cheapest Chicago to Boston flights over the next 3 months. One-way fares from TRY 4,659, return fares from TRY 4,659.

    • Cheapest
      MDW 20:35
      11h 58m
      1 stop
      BOS 09:33
      Chicago - Boston | Mon, Dec 21 | Frontier Airlines
      TRY 4,659 TRY 8,235
      43% off
      43% off
      TRY 8,235 TRY 4,659
    • MDW 06:00
      8h 1m
      1 stop
      BOS 15:01
      Chicago - Boston | Fri, Nov 27 | Delta Air Lines
      TRY 5,032 TRY 8,235
      39% off
      39% off
      TRY 8,235 TRY 5,032
    • MDW 09:30
      5h 22m
      1 stop
      BOS 15:52
      Chicago - Boston | Fri, Nov 20 | Delta Air Lines
      TRY 5,398 TRY 8,235
      34% off
      34% off
      TRY 8,235 TRY 5,398
    • MDW 13:41
      5h 16m
      1 stop
      BOS 19:57
      Chicago - Boston | Tue, Dec 8 | Delta Air Lines
      TRY 5,555
      33% off
      TRY 8,235 TRY 5,555
    • MDW 17:29
      5h 15m
      1 stop
      BOS 23:44
      Chicago - Boston | Sun, Nov 15 | Delta Air Lines
      TRY 5,555
      33% off
      TRY 8,235 TRY 5,555
    • MDW 18:41
      4h 17m
      1 stop
      BOS 23:58
      Chicago - Boston | Sun, Dec 6 | Delta Air Lines
      TRY 5,615
      32% off
      TRY 8,235 TRY 5,615
    • CHI 13:00
      17h 25m
      1 stop
      BOS 14:00
      Chicago - Boston | Sun, Oct 25 | Normal Airline
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    • MDW 18:15
      4h 44m
      1 stop
      BOS 23:59
      Chicago - Boston | Fri, Jan 1 | Delta Air Lines
      TRY 8,205 TRY 14,292
      43% off
      43% off
      TRY 14,292 TRY 8,205
    • CHI 13:00
      17h 25m
      1 stop
      BOS 14:00
      Chicago - Boston | Sun, Oct 25 | Normal Airline
      Find more flights
      Find more flights
    • MDW 18:41
      4h 17m
      1 stop
      BOS 23:58
      Chicago - Boston | Sun, Dec 6 | Delta Air Lines
      TRY 5,615 TRY 8,235
      32% off
      32% off
      TRY 8,235 TRY 5,615
    • MDW 17:29
      5h 15m
      1 stop
      BOS 23:44
      Chicago - Boston | Sun, Nov 15 | Delta Air Lines
      TRY 5,555 TRY 8,235
      33% off
      33% off
      TRY 8,235 TRY 5,555
    • MDW 13:41
      5h 16m
      1 stop
      BOS 19:57
      Chicago - Boston | Tue, Dec 8 | Delta Air Lines
      TRY 5,555 TRY 8,235
      33% off
      33% off
      TRY 8,235 TRY 5,555
    • MDW 09:30
      5h 22m
      1 stop
      BOS 15:52
      Chicago - Boston | Fri, Nov 20 | Delta Air Lines
      TRY 5,398
      34% off
      TRY 8,235 TRY 5,398
    • MDW 06:00
      8h 1m
      1 stop
      BOS 15:01
      Chicago - Boston | Fri, Nov 27 | Delta Air Lines
      TRY 5,032
      39% off
      TRY 8,235 TRY 5,032
    • MDW 20:35
      11h 58m
      1 stop
      BOS 09:33
      Chicago - Boston | Mon, Dec 21 | Frontier Airlines
      TRY 4,659
      43% off
      TRY 8,235 TRY 4,659
    • CHI 13:00
      17h 25m
      1 stop
      BOS 14:00
      Chicago - Boston | Sun, Oct 25 | Normal Airline
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      Find more flights

Displayed flight fares from Chicago to Boston 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 Chicago Midway International Airport to Boston Logan International Airport?

The cheapest airline flying from Chicago Midway International Airport to Boston Logan International Airport is Frontier Airlines (from TRY 5,107) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Frontier Airlines
From TRY 5,107
Delta Air Lines
From TRY 5,308
Hahn Air
From TRY 9,034

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

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

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL4688

    Chicago Midway International Airport

    13:27

    MDW

    1h 15m

    Direct

    15:42

    DTW

    S M T W T F S
    Search

  2. DL1707

    Detroit Metropolitan Wayne County Airport

    17:45

    DTW

    2h

    Direct

    19:45

    BOS

    S M T W T - S

  3. DL1063

    Chicago Midway International Airport

    10:59

    MDW

    1h 54m

    Direct

    13:53

    ATL

    S M T W T F S
    Search

  4. DL2595

    Hartsfield–Jackson Atlanta International Airport

    15:10

    ATL

    2h 38m

    Direct

    17:48

    BOS

    S M T - - F S

  5. DL1285

    Chicago Midway International Airport

    06:00

    MDW

    2h

    Direct

    09:00

    ATL

    S M T W T F S
    Search

  6. DL862

    Hartsfield–Jackson Atlanta International Airport

    11:10

    ATL

    2h 34m

    Direct

    13:44

    BOS

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

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

Flight distance 1,380.83km
Cheapest one-way ticket price TRY 4,659

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

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

    Chicago Midway International Airport to Boston Logan International Airport takes about 2 hours 4 minutes on average. Actual flight time may vary depending on route, weather and air traffic.
  • There are around 4 daily flights from Chicago Midway International Airport (MDW) to Boston Logan International Airport (BOS).
  • The earliest flight from Chicago Midway International Airport to Boston Logan International Airport departs at 05:00, and the last departs at 19:00, with about 15 flights per day. Flight times may change, so please check the latest departure and arrival times before you travel.
  • The route from Chicago Midway International Airport (MDW) to Boston Logan International Airport (BOS) is quite popular. Without considering departure times or holidays, tickets cost around TRY 11,214 in October, the most expensive month to book this route.
  • Based on Trip.com flight data for departures within the next 30 days with at most one stop, the average one-way price from Chicago Midway International Airport to Boston Logan International Airport is TRY 8,231. Prices may vary depending on the departure date, airline, and availability.
  • Jetblue Airways are the most popular budget airlines flying from Chicago Midway International Airport to Boston Logan International Airport, with one-way fares starting from TRY 4,659. Compare final prices carefully, as baggage, seat selection and payment fees may apply.
  • Enter Chicago Midway International Airport and Boston Logan 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.

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Prices displayed on this page are all-inclusive (including taxes, fuel surcharges, civil aviation development fund, etc.), with all fees confirmed before payment. Fees for luggage, 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 have been updated within the last 24 hours—sometimes even in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the cancellation and change policies for each flight ticket during the booking process, including any fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply according to the airline's ticket policy.
Cancellation/change due to a flight schedule change:
If the flight schedule has changed 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 visit the customer support pages.