Travel with Axel,
get the best price.

Boston → Chicago

Choose your travel dates

BOS → MDW1 adulteconomy

21 flight options · 3 airlines

Round-trip flights

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:30 pmBOS
2h 45m
Nonstop
8:15 pmMDW
Southwest Airlines
1:00 pmMDW
2h 10m
Nonstop
4:10 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Frontier Airlines
12:15 pmBOS
6h 32m
ATL · 1h 9m
5:47 pmMDW
Southwest Airlines
1:00 pmMDW
2h 10m
Nonstop
4:10 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:10 amBOS
2h 45m
Nonstop
8:55 amMDW
Southwest Airlines
1:00 pmMDW
2h 10m
Nonstop
4:10 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Frontier Airlines
12:15 pmBOS
6h 32m
ATL · 1h 9m
5:47 pmMDW
Southwest Airlines
1:15 pmMDW
2h 5m
Nonstop
4:20 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
5:35 amBOS
7h 30m
STL · 3h 15m
12:05 pmMDW
Southwest Airlines
1:00 pmMDW
2h 10m
Nonstop
4:10 pmBOS

Round-trip total · 1 adult · Taxes included

Show 6 more flights

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:25 pmBOS
7h 40m
BNA · 3h 15m
9:05 pmMDW
Southwest Airlines
1:00 pmMDW
2h 10m
Nonstop
4:10 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:25 amBOS
5h 50m
BWI · 1h 50m
12:15 pmMDW
Southwest Airlines
1:00 pmMDW
2h 10m
Nonstop
4:10 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
7:25 amBOS
5h 50m
BWI · 1h 50m
12:15 pmMDW
Southwest Airlines
1:15 pmMDW
2h 5m
Nonstop
4:20 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
2:25 pmBOS
7h 40m
BNA · 3h 15m
9:05 pmMDW
Southwest Airlines
1:15 pmMDW
2h 5m
Nonstop
4:20 pmBOS

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
6:30 pmBOS
2h 45m
Nonstop
8:15 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Frontier Airlines
12:15 pmBOS
6h 32m
ATL · 1h 9m
5:47 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
1:04 pmBOS
5h 57m
DTW · 2h 21m
6:01 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:10 amBOS
2h 45m
Nonstop
8:55 amMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
5:35 amBOS
7h 30m
STL · 3h 15m
12:05 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:25 pmBOS
7h 40m
BNA · 3h 15m
9:05 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:25 amBOS
5h 50m
BWI · 1h 50m
12:15 pmMDW

One-way total · 1 adult · Taxes included

Make this trip yours

BOS ⇄ MDW

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.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. 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

More dates

Nov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-11-20 · one waySouthwest AirlinesWN816$189.002026-10-29T00:52:27Z
2026-11-27 → 2026-12-04Southwest AirlinesWN816 / WN2900$317.252026-10-29T00:52:27Z
2026-11-20 · one wayFrontier AirlinesF93511 + F92779$128.252026-10-29T00:52:27Z
2026-11-20 · one wayDelta Air LinesDL2222 + DL4677$249.752026-10-29T00:52:27Z
2026-11-27 → 2026-12-04Frontier Airlines / Southwest AirlinesF93511 + F92779 / WN2900$256.502026-10-29T00:52:27Z
2026-11-27 → 2026-12-04Delta Air LinesDL2222 + DL4677 / DL5469 + DL2558$411.252026-10-29T00:52:27Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4995 / WN2900$364.502026-10-29T00:52:27Z
2026-11-20 · one waySouthwest AirlinesWN4995$189.002026-10-29T00:52:27Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4995 / WN2900$317.252026-10-29T00:52:27Z
2026-11-20 → 2026-11-23Southwest AirlinesWN816 / WN2900$364.502026-10-29T00:52:27Z
2026-11-20 · one waySouthwest AirlinesWN819 + WN287$202.502026-10-29T00:52:27Z
2026-11-20 · one waySouthwest AirlinesWN4765 + WN651$202.502026-10-29T00:52:27Z
2026-11-20 · one waySouthwest AirlinesWN1426 + WN1070$202.502026-10-29T00:52:27Z
2026-11-20 → 2026-11-23Frontier Airlines / Southwest AirlinesF93511 + F92779 / WN2900$303.752026-10-29T00:52:27Z
2026-11-27 → 2026-12-04Southwest AirlinesWN819 + WN287 / WN2900$330.752026-10-29T00:52:27Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4765 + WN651 / WN2900$330.752026-10-29T00:52:27Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1426 + WN1070 / WN2900$330.752026-10-29T00:52:27Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1426 + WN1070 / WN2900$378.002026-10-29T00:52:27Z
2026-11-20 → 2026-11-23Southwest AirlinesWN819 + WN287 / WN2900$378.002026-10-29T00:52:27Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4765 + WN651 / WN2900$378.002026-10-29T00:52:27Z
2026-11-20 → 2026-11-23Delta Air LinesDL2222 + DL4677 / DL5469 + DL2558$472.502026-10-29T00:52:27Z

2026-11-20 · one way · $189.00

  • Southwest Airlines WN816: BOS 2026-11-20 18:30:00 → MDW 2026-11-20 20:15:00; nonstop; 165 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $317.25

  • Southwest Airlines WN816: BOS 2026-11-27 18:30:00 → MDW 2026-11-27 20:15:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-20 · one way · $128.25

  • Frontier Airlines F93511 / F92779: BOS 2026-11-20 12:15:00 → MDW 2026-11-20 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
    • F93511: BOS 2026-11-20 12:15:00 → ATL 2026-11-20 15:36:00; layover at ATL: 69 minutes.
    • F92779: ATL 2026-11-20 16:45:00 → MDW 2026-11-20 17:47:00.

2026-11-20 · one way · $249.75

  • Delta Air Lines DL2222 / DL4677: BOS 2026-11-20 13:04:00 → MDW 2026-11-20 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-11-20 13:04:00 → DTW 2026-11-20 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-11-20 17:40:00 → MDW 2026-11-20 18:01:00.

2026-11-27 → 2026-12-04 · $256.50

  • Frontier Airlines F93511 / F92779: BOS 2026-11-27 12:15:00 → MDW 2026-11-27 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
    • F93511: BOS 2026-11-27 12:15:00 → ATL 2026-11-27 15:36:00; layover at ATL: 69 minutes.
    • F92779: ATL 2026-11-27 16:45:00 → MDW 2026-11-27 17:47:00.
  • Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $411.25

  • Delta Air Lines DL2222 / DL4677: BOS 2026-11-27 13:04:00 → MDW 2026-11-27 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-11-27 13:04:00 → DTW 2026-11-27 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-11-27 17:40:00 → MDW 2026-11-27 18:01:00.
  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-04 10:24:00 → BOS 2026-12-04 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-04 10:24:00 → MSP 2026-12-04 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-04 13:09:00 → BOS 2026-12-04 17:01:00.

2026-11-20 → 2026-11-23 · $364.50

  • Southwest Airlines WN4995: BOS 2026-11-20 07:10:00 → MDW 2026-11-20 08:55:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2900: MDW 2026-11-23 13:15:00 → BOS 2026-11-23 16:20:00; nonstop; 125 minutes. Local airport times.

2026-11-20 · one way · $189.00

  • Southwest Airlines WN4995: BOS 2026-11-20 07:10:00 → MDW 2026-11-20 08:55:00; nonstop; 165 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $317.25

  • Southwest Airlines WN4995: BOS 2026-11-27 07:10:00 → MDW 2026-11-27 08:55:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $364.50

  • Southwest Airlines WN816: BOS 2026-11-20 18:30:00 → MDW 2026-11-20 20:15:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2900: MDW 2026-11-23 13:15:00 → BOS 2026-11-23 16:20:00; nonstop; 125 minutes. Local airport times.

2026-11-20 · one way · $202.50

  • Southwest Airlines WN819 / WN287: BOS 2026-11-20 05:35:00 → MDW 2026-11-20 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-11-20 05:35:00 → STL 2026-11-20 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-11-20 10:55:00 → MDW 2026-11-20 12:05:00.

2026-11-20 · one way · $202.50

  • Southwest Airlines WN4765 / WN651: BOS 2026-11-20 14:25:00 → MDW 2026-11-20 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
    • WN4765: BOS 2026-11-20 14:25:00 → BNA 2026-11-20 16:15:00; layover at BNA: 195 minutes.
    • WN651: BNA 2026-11-20 19:30:00 → MDW 2026-11-20 21:05:00.

2026-11-20 · one way · $202.50

  • Southwest Airlines WN1426 / WN1070: BOS 2026-11-20 07:25:00 → MDW 2026-11-20 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN1426: BOS 2026-11-20 07:25:00 → BWI 2026-11-20 09:15:00; layover at BWI: 110 minutes.
    • WN1070: BWI 2026-11-20 11:05:00 → MDW 2026-11-20 12:15:00.

2026-11-20 → 2026-11-23 · $303.75

  • Frontier Airlines F93511 / F92779: BOS 2026-11-20 12:15:00 → MDW 2026-11-20 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
    • F93511: BOS 2026-11-20 12:15:00 → ATL 2026-11-20 15:36:00; layover at ATL: 69 minutes.
    • F92779: ATL 2026-11-20 16:45:00 → MDW 2026-11-20 17:47:00.
  • Southwest Airlines WN2900: MDW 2026-11-23 13:15:00 → BOS 2026-11-23 16:20:00; nonstop; 125 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $330.75

  • Southwest Airlines WN819 / WN287: BOS 2026-11-27 05:35:00 → MDW 2026-11-27 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-11-27 05:35:00 → STL 2026-11-27 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-11-27 10:55:00 → MDW 2026-11-27 12:05:00.
  • Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $330.75

  • Southwest Airlines WN4765 / WN651: BOS 2026-11-27 14:25:00 → MDW 2026-11-27 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
    • WN4765: BOS 2026-11-27 14:25:00 → BNA 2026-11-27 16:15:00; layover at BNA: 195 minutes.
    • WN651: BNA 2026-11-27 19:30:00 → MDW 2026-11-27 21:05:00.
  • Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $330.75

  • Southwest Airlines WN1426 / WN1070: BOS 2026-11-27 07:25:00 → MDW 2026-11-27 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN1426: BOS 2026-11-27 07:25:00 → BWI 2026-11-27 09:15:00; layover at BWI: 110 minutes.
    • WN1070: BWI 2026-11-27 11:05:00 → MDW 2026-11-27 12:15:00.
  • Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $378.00

  • Southwest Airlines WN1426 / WN1070: BOS 2026-11-20 07:25:00 → MDW 2026-11-20 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN1426: BOS 2026-11-20 07:25:00 → BWI 2026-11-20 09:15:00; layover at BWI: 110 minutes.
    • WN1070: BWI 2026-11-20 11:05:00 → MDW 2026-11-20 12:15:00.
  • Southwest Airlines WN2900: MDW 2026-11-23 13:15:00 → BOS 2026-11-23 16:20:00; nonstop; 125 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $378.00

  • Southwest Airlines WN819 / WN287: BOS 2026-11-20 05:35:00 → MDW 2026-11-20 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-11-20 05:35:00 → STL 2026-11-20 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-11-20 10:55:00 → MDW 2026-11-20 12:05:00.
  • Southwest Airlines WN2900: MDW 2026-11-23 13:15:00 → BOS 2026-11-23 16:20:00; nonstop; 125 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $378.00

  • Southwest Airlines WN4765 / WN651: BOS 2026-11-20 14:25:00 → MDW 2026-11-20 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
    • WN4765: BOS 2026-11-20 14:25:00 → BNA 2026-11-20 16:15:00; layover at BNA: 195 minutes.
    • WN651: BNA 2026-11-20 19:30:00 → MDW 2026-11-20 21:05:00.
  • Southwest Airlines WN2900: MDW 2026-11-23 13:15:00 → BOS 2026-11-23 16:20:00; nonstop; 125 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $472.50

  • Delta Air Lines DL2222 / DL4677: BOS 2026-11-20 13:04:00 → MDW 2026-11-20 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-11-20 13:04:00 → DTW 2026-11-20 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-11-20 17:40:00 → MDW 2026-11-20 18:01:00.
  • Delta Air Lines DL5469 / DL2558: MDW 2026-11-23 10:24:00 → BOS 2026-11-23 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-11-23 10:24:00 → MSP 2026-11-23 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-11-23 13:09:00 → BOS 2026-11-23 17:01:00.

More dates for this route