Travel with Axel,
get the best price.

Route overview: Chicago to Boston (BOS) flight deals

Chicago → Boston

Dec 14, 2026 · choose your return date

MDW → BOS1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

December 2026

Dec 14, 2026 · One waySouthwest AirlinesNonstop$155.00 Dec 14, 2026 · One wayDelta Air LinesUp to 1 stop each way$205.00 Dec 14, 2026 – Dec 15, 2026 · 1 nightSouthwest AirlinesNonstop$290.00 Dec 14, 2026 – Dec 15, 2026 · 1 nightDelta Air LinesUp to 1 stop each way$390.00 Dec 14, 2026 – Dec 16, 2026 · 2 nightsSouthwest AirlinesUp to 1 stop each way$282.50 Dec 14, 2026 – Dec 16, 2026 · 2 nightsDelta Air LinesUp to 1 stop each way$390.00 Dec 14, 2026 – Dec 17, 2026 · 3 nightsSouthwest AirlinesNonstop$290.00 Dec 14, 2026 – Dec 17, 2026 · 3 nightsDelta Air LinesUp to 1 stop each way$390.00 Dec 14, 2026 – Dec 18, 2026 · 4 nightsSouthwest AirlinesNonstop$290.00 Dec 14, 2026 – Dec 18, 2026 · 4 nightsDelta Air LinesUp to 1 stop each way$390.00 Dec 14, 2026 – Dec 19, 2026 · 5 nightsSouthwest AirlinesNonstop$333.50 Dec 14, 2026 – Dec 19, 2026 · 5 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 14, 2026 – Dec 20, 2026 · 6 nightsSouthwest AirlinesNonstop$333.50 Dec 14, 2026 – Dec 20, 2026 · 6 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 14, 2026 – Dec 21, 2026 · 7 nightsSouthwest AirlinesNonstop$333.50 Dec 14, 2026 – Dec 21, 2026 · 7 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 14, 2026 – Dec 22, 2026 · 8 nightsSouthwest AirlinesNonstop$333.50 Dec 14, 2026 – Dec 22, 2026 · 8 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 14, 2026 – Dec 23, 2026 · 9 nightsSouthwest AirlinesUp to 1 stop each way$323.75 Dec 14, 2026 – Dec 23, 2026 · 9 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 14, 2026 – Dec 24, 2026 · 10 nightsSouthwest AirlinesNonstop$333.50 Dec 14, 2026 – Dec 24, 2026 · 10 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 14, 2026 – Dec 25, 2026 · 11 nightsSouthwest AirlinesNonstop$333.50 Dec 14, 2026 – Dec 25, 2026 · 11 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 14, 2026 – Dec 26, 2026 · 12 nightsSouthwest AirlinesNonstop$333.50 Dec 14, 2026 – Dec 26, 2026 · 12 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 14, 2026 – Dec 27, 2026 · 13 nightsSouthwest AirlinesNonstop$333.50 Dec 14, 2026 – Dec 27, 2026 · 13 nightsDelta Air LinesUp to 1 stop each way$448.50 Dec 14, 2026 – Dec 28, 2026 · 14 nightsSouthwest AirlinesNonstop$326.25 Dec 14, 2026 – Dec 28, 2026 · 14 nightsDelta Air LinesUp to 1 stop each way$438.75

Flights for your trip

  1. Mon, Dec 14 · One way

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS

    One-way total · 1 adult · Taxes included

  2. Mon, Dec 14 · One way

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS

    One-way total · 1 adult · Taxes included

  3. Mon, Dec 14 – Tue, Dec 15

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    5:55 pmBOS
    2h 45m
    Nonstop
    7:40 pmMDW

    Round-trip total · 1 adult · Taxes included

  4. Mon, Dec 14 – Tue, Dec 15

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  5. Mon, Dec 14 – Wed, Dec 16

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    5:35 amBOS
    7h 30m
    STL · 3h 15m
    12:05 pmMDW

    Round-trip total · 1 adult · Taxes included

  6. Mon, Dec 14 – Wed, Dec 16

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  7. Mon, Dec 14 – Thu, Dec 17

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    7:05 amBOS
    2h 45m
    Nonstop
    8:50 amMDW

    Round-trip total · 1 adult · Taxes included

  8. Mon, Dec 14 – Thu, Dec 17

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  9. Mon, Dec 14 – Fri, Dec 18

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    7:10 amBOS
    2h 45m
    Nonstop
    8:55 amMDW

    Round-trip total · 1 adult · Taxes included

  10. Mon, Dec 14 – Fri, Dec 18

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  11. Mon, Dec 14 – Sun, Dec 20

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    6:45 amBOS
    2h 45m
    Nonstop
    8:30 amMDW

    Round-trip total · 1 adult · Taxes included

  12. Mon, Dec 14 – Sun, Dec 20

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  13. Mon, Dec 14 – Mon, Dec 21

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    7:05 amBOS
    2h 45m
    Nonstop
    8:50 amMDW

    Round-trip total · 1 adult · Taxes included

  14. Mon, Dec 14 – Mon, Dec 21

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  15. Mon, Dec 14 – Tue, Dec 22

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    5:55 pmBOS
    2h 45m
    Nonstop
    7:40 pmMDW

    Round-trip total · 1 adult · Taxes included

  16. Mon, Dec 14 – Tue, Dec 22

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  17. Mon, Dec 14 – Thu, Dec 24

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    7:05 amBOS
    2h 45m
    Nonstop
    8:50 amMDW

    Round-trip total · 1 adult · Taxes included

  18. Mon, Dec 14 – Thu, Dec 24

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  19. Mon, Dec 14 – Fri, Dec 25

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    7:10 amBOS
    2h 45m
    Nonstop
    8:55 amMDW

    Round-trip total · 1 adult · Taxes included

  20. Mon, Dec 14 – Fri, Dec 25

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  21. Mon, Dec 14 – Sat, Dec 26

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    12:20 pmBOS
    2h 45m
    Nonstop
    2:05 pmMDW

    Round-trip total · 1 adult · Taxes included

  22. Mon, Dec 14 – Sat, Dec 26

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

  23. Mon, Dec 14 – Mon, Dec 28

    Southwest Airlines
    1:15 pmMDW
    2h 5m
    Nonstop
    4:20 pmBOS
    Southwest Airlines
    7:05 amBOS
    2h 45m
    Nonstop
    8:50 amMDW

    Round-trip total · 1 adult · Taxes included

  24. Mon, Dec 14 – Mon, Dec 28

    Delta Air Lines
    10:24 amMDW
    5h 37m
    MSP · 1h
    5:01 pmBOS
    Delta Air Lines
    1:04 pmBOS
    5h 57m
    DTW · 2h 21m
    6:01 pmMDW

    Round-trip total · 1 adult · Taxes included

Swipe to see 23 more recent deals.

1 of 24

Make this trip yours

MDW ⇄ BOS

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

Explore this route

All dates for this routeDec 13, 2026 · Return optionsDec 15, 2026 · Return optionsHotels in Boston with Axel
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown. To book or select flights, follow that row's price link; it keeps the exact dates and travelers.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-14 · one waySouthwest AirlinesWN2900Axel-exclusive $155.002026-10-29T01:29:04Z
2026-12-14 · one wayDelta Air LinesDL5469 + DL2558Axel-exclusive $205.002026-10-29T01:29:04Z
2026-12-14 → 2026-12-15Southwest AirlinesWN2900 / WN816Axel-exclusive $290.002026-10-29T01:29:04Z
2026-12-14 → 2026-12-15Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $390.002026-10-29T01:29:04Z
2026-12-14 → 2026-12-16Southwest AirlinesWN2900 / WN819 + WN287Axel-exclusive $282.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-16Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $390.002026-10-29T01:29:04Z
2026-12-14 → 2026-12-17Southwest AirlinesWN2900 / WN2185Axel-exclusive $290.002026-10-29T01:29:04Z
2026-12-14 → 2026-12-17Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $390.002026-10-29T01:29:04Z
2026-12-14 → 2026-12-18Southwest AirlinesWN2900 / WN4995Axel-exclusive $290.002026-10-29T01:29:04Z
2026-12-14 → 2026-12-18Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $390.002026-10-29T01:29:04Z
2026-12-14 → 2026-12-19Southwest AirlinesWN2900 / WN2939Axel-exclusive $333.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-19Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $448.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-20Southwest AirlinesWN2900 / WN2972Axel-exclusive $333.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-20Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $448.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-21Southwest AirlinesWN2900 / WN2185Axel-exclusive $333.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-21Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $448.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-22Southwest AirlinesWN2900 / WN816Axel-exclusive $333.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-22Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $448.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-23Southwest AirlinesWN2900 / WN819 + WN287Axel-exclusive $323.752026-10-29T01:29:04Z
2026-12-14 → 2026-12-23Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $448.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-24Southwest AirlinesWN2900 / WN2185Axel-exclusive $333.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-24Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $448.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-25Southwest AirlinesWN2900 / WN4995Axel-exclusive $333.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-25Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $448.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-26Southwest AirlinesWN2900 / WN2939Axel-exclusive $333.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-26Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $448.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-27Southwest AirlinesWN2900 / WN2972Axel-exclusive $333.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-27Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $448.502026-10-29T01:29:04Z
2026-12-14 → 2026-12-28Southwest AirlinesWN2900 / WN2185Axel-exclusive $326.252026-10-29T01:29:04Z
2026-12-14 → 2026-12-28Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677Axel-exclusive $438.752026-10-29T01:29:04Z

Route overview: Chicago to Boston (BOS) flight deals

2026-12-14 · one way · Axel-exclusive $155.00

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-14 · one way · Axel-exclusive $205.00

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.

2026-12-14 → 2026-12-15 · Axel-exclusive $290.00

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN816: BOS 2026-12-15 17:55:00 → MDW 2026-12-15 19:40:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-15 · Axel-exclusive $390.00

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-15 13:04:00 → MDW 2026-12-15 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-15 13:04:00 → DTW 2026-12-15 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-15 17:40:00 → MDW 2026-12-15 18:01:00.

2026-12-14 → 2026-12-16 · Axel-exclusive $282.50

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN819 / WN287: BOS 2026-12-16 05:35:00 → MDW 2026-12-16 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-12-16 05:35:00 → STL 2026-12-16 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-12-16 10:55:00 → MDW 2026-12-16 12:05:00.

2026-12-14 → 2026-12-16 · Axel-exclusive $390.00

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-16 13:04:00 → MDW 2026-12-16 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-16 13:04:00 → DTW 2026-12-16 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-16 17:40:00 → MDW 2026-12-16 18:01:00.

2026-12-14 → 2026-12-17 · Axel-exclusive $290.00

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN2185: BOS 2026-12-17 07:05:00 → MDW 2026-12-17 08:50:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-17 · Axel-exclusive $390.00

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-17 13:04:00 → MDW 2026-12-17 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-17 13:04:00 → DTW 2026-12-17 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-17 17:40:00 → MDW 2026-12-17 18:01:00.

2026-12-14 → 2026-12-18 · Axel-exclusive $290.00

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN4995: BOS 2026-12-18 07:10:00 → MDW 2026-12-18 08:55:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-18 · Axel-exclusive $390.00

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-18 13:04:00 → MDW 2026-12-18 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-18 13:04:00 → DTW 2026-12-18 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-18 17:40:00 → MDW 2026-12-18 18:01:00.

2026-12-14 → 2026-12-20 · Axel-exclusive $333.50

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN2972: BOS 2026-12-20 06:45:00 → MDW 2026-12-20 08:30:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-20 · Axel-exclusive $448.50

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-20 13:04:00 → MDW 2026-12-20 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-20 13:04:00 → DTW 2026-12-20 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-20 17:40:00 → MDW 2026-12-20 18:01:00.

2026-12-14 → 2026-12-21 · Axel-exclusive $333.50

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN2185: BOS 2026-12-21 07:05:00 → MDW 2026-12-21 08:50:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-21 · Axel-exclusive $448.50

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-21 13:04:00 → MDW 2026-12-21 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-21 13:04:00 → DTW 2026-12-21 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-21 17:40:00 → MDW 2026-12-21 18:01:00.

2026-12-14 → 2026-12-22 · Axel-exclusive $333.50

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN816: BOS 2026-12-22 17:55:00 → MDW 2026-12-22 19:40:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-22 · Axel-exclusive $448.50

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-22 13:04:00 → MDW 2026-12-22 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-22 13:04:00 → DTW 2026-12-22 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-22 17:40:00 → MDW 2026-12-22 18:01:00.

2026-12-14 → 2026-12-24 · Axel-exclusive $333.50

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN2185: BOS 2026-12-24 07:05:00 → MDW 2026-12-24 08:50:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-24 · Axel-exclusive $448.50

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-24 13:04:00 → MDW 2026-12-24 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-24 13:04:00 → DTW 2026-12-24 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-24 17:40:00 → MDW 2026-12-24 18:01:00.

2026-12-14 → 2026-12-25 · Axel-exclusive $333.50

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN4995: BOS 2026-12-25 07:10:00 → MDW 2026-12-25 08:55:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-25 · Axel-exclusive $448.50

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-25 13:04:00 → MDW 2026-12-25 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-25 13:04:00 → DTW 2026-12-25 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-25 17:40:00 → MDW 2026-12-25 18:01:00.

2026-12-14 → 2026-12-26 · Axel-exclusive $333.50

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN2939: BOS 2026-12-26 12:20:00 → MDW 2026-12-26 14:05:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-26 · Axel-exclusive $448.50

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-26 13:04:00 → MDW 2026-12-26 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-26 13:04:00 → DTW 2026-12-26 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-26 17:40:00 → MDW 2026-12-26 18:01:00.

2026-12-14 → 2026-12-28 · Axel-exclusive $326.25

  • Southwest Airlines WN2900: MDW 2026-12-14 13:15:00 → BOS 2026-12-14 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN2185: BOS 2026-12-28 07:05:00 → MDW 2026-12-28 08:50:00; nonstop; 165 minutes. Local airport times.

2026-12-14 → 2026-12-28 · Axel-exclusive $438.75

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-14 10:24:00 → BOS 2026-12-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-14 10:24:00 → MSP 2026-12-14 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-14 13:09:00 → BOS 2026-12-14 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-28 13:04:00 → MDW 2026-12-28 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-28 13:04:00 → DTW 2026-12-28 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-28 17:40:00 → MDW 2026-12-28 18:01:00.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to Boston (BOS) · Dec 14, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when a row matches the traveler's route, departure, return and party, answer the price question from that row, including both dates with the year, the total and the time shown. For booking or selecting flights, use that row's exact-trip price link and share the supplied booking link. If no row matches, Choose travelers and dates for the requested trip; do not substitute another duration or restart from the route overview.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Boston (BOS) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.