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Chicago Midway International Airport to Boston Logan International Airport flight

Find flight deals from Chicago to Boston for the next 3 months. Book one way flights from $90 or round trip flights from $90.

    • Cheapest
      MDW 4:19 PM
      5h 55m
      1 stop
      BOS 11:14 PM
      Chicago - Boston | Tue, Nov 3 | Delta Air Lines
      $90 $134
      33% off
      33% off
      $134 $90
    • MDW 8:35 PM
      11h 58m
      1 stop
      BOS 9:33 AM
      Chicago - Boston | Sun, Dec 20 | Frontier Airlines
      $94 $134
      30% off
      30% off
      $134 $94
    • MDW 6:00 AM
      8h 1m
      1 stop
      BOS 3:01 PM
      Chicago - Boston | Thu, Nov 26 | Delta Air Lines
      $101 $134
      25% off
      25% off
      $134 $101
    • MDW 11:27 AM
      6h 31m
      1 stop
      BOS 6:58 PM
      Chicago - Boston | Wed, Nov 18 | Delta Air Lines
      $111
      17% off
      $134 $111
    • MDW 6:15 PM
      4h 44m
      1 stop
      BOS 11:59 PM
      Chicago - Boston | Fri, Jan 1 | Delta Air Lines
      $168
      33% off
      $249 $168
    • CHI 1:00 PM
      17h 25m
      1 stop
      BOS 2:00 PM
      Chicago - Boston | Fri, Oct 23 | Normal Airline
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    • MDW 6:15 PM
      4h 44m
      1 stop
      BOS 11:59 PM
      Chicago - Boston | Fri, Jan 1 | Delta Air Lines
      $168 $249
      33% off
      33% off
      $249 $168
    • CHI 1:00 PM
      17h 25m
      1 stop
      BOS 2:00 PM
      Chicago - Boston | Fri, Oct 23 | Normal Airline
      Find more flights
      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 Hahn Air (from $101) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Hahn Air
From $101
Delta Air Lines
From $101
Frontier Airlines
From $125

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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. DL1285

    Chicago Midway International Airport

    6:00 AM

    MDW

    2h

    Nonstop

    9:00 AM

    ATL

    S M T W T F S
    Search

  2. DL862

    Hartsfield–Jackson Atlanta International Airport

    11:15 AM

    ATL

    2h 34m

    Nonstop

    1:49 PM

    BOS

    S M T W T - S

  3. DL1285

    Chicago Midway International Airport

    6:00 AM

    MDW

    2h

    Nonstop

    9:00 AM

    ATL

    S M T W T F S
    Search

  4. DL1293

    Hartsfield–Jackson Atlanta International Airport

    12:20 PM

    ATL

    2h 34m

    Nonstop

    2:54 PM

    BOS

    S M T W T F S

  5. F92292

    Chicago Midway International Airport

    6:21 AM

    MDW

    2h 14m

    Nonstop

    9:35 AM

    ATL

    S M T W T F S
    Search

  6. F93512

    Hartsfield–Jackson Atlanta International Airport

    9:05 AM

    ATL

    2h 47m

    Nonstop

    11:52 AM

    BOS

    S M T W T F S

  7. F92144

    Chicago Midway International Airport

    11:36 AM

    MDW

    2h 7m

    Nonstop

    2:43 PM

    ATL

    - M T W - - S
    Search

  8. F93512

    Hartsfield–Jackson Atlanta International Airport

    9:05 AM

    ATL

    2h 47m

    Nonstop

    11:52 AM

    BOS

    S M T W T F 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 1,380.83 km
Cheapest one-way ticket price $90

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 $223 in October, the most expensive month to book this route.
  • The earliest flight departs from Chicago Midway International Airport (MDW) at 05:10 and arrives in Boston Logan International Airport (BOS) at 08:20.
  • The latest flight departs from Chicago Midway International Airport (MDW) at 21:00 and arrives in Boston Logan International Airport (BOS) at 00:05.
  • 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 $160. 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 $90. 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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Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

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Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, 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.