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Route overview: Boston to Chicago (MDW) flight deals

Boston → Chicago

Feb 5, 2027 · return Feb 8, 2027

BOS → MDW1 adulteconomyRound trip

7 flight options · 3 airlines

Nonstop flights

Fri, Feb 5 – Mon, Feb 8

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, Feb 5 – Mon, Feb 8

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

One-stop flights

Fri, Feb 5 – Mon, Feb 8

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, Feb 5 – Mon, Feb 8

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, Feb 5 – Mon, Feb 8

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, Feb 5 – Mon, Feb 8

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, Feb 5 – Mon, Feb 8

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

Make this trip yours

BOS ⇄ MDW

Economy

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

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Explore this route

All dates for this routeFeb 4, 2027 → Feb 7, 2027Feb 6, 2027 → Feb 9, 2027
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.

Route overview: Boston to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-02-05 → 2027-02-08Southwest AirlinesWN816 / WN2900$270.002026-10-29T00:52:27Z
2027-02-05 → 2027-02-08Frontier Airlines / Southwest AirlinesF93511 + F92779 / WN2900$225.002026-10-29T00:52:27Z
2027-02-05 → 2027-02-08Delta Air LinesDL2222 + DL4677 / DL5469 + DL2558$350.002026-10-29T00:52:27Z
2027-02-05 → 2027-02-08Southwest AirlinesWN4995 / WN2900$270.002026-10-29T00:52:27Z
2027-02-05 → 2027-02-08Southwest AirlinesWN4765 + WN651 / WN2900$280.002026-10-29T00:52:27Z
2027-02-05 → 2027-02-08Southwest AirlinesWN819 + WN287 / WN2900$280.002026-10-29T00:52:27Z
2027-02-05 → 2027-02-08Southwest AirlinesWN1426 + WN1070 / WN2900$280.002026-10-29T00:52:27Z

2027-02-05 → 2027-02-08 · $270.00

  • Southwest Airlines WN816: BOS 2027-02-05 18:30:00 → MDW 2027-02-05 20:15:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2900: MDW 2027-02-08 13:15:00 → BOS 2027-02-08 16:20:00; nonstop; 125 minutes. Local airport times.

2027-02-05 → 2027-02-08 · $225.00

  • Frontier Airlines F93511 / F92779: BOS 2027-02-05 12:15:00 → MDW 2027-02-05 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
    • F93511: BOS 2027-02-05 12:15:00 → ATL 2027-02-05 15:36:00; layover at ATL: 69 minutes.
    • F92779: ATL 2027-02-05 16:45:00 → MDW 2027-02-05 17:47:00.
  • Southwest Airlines WN2900: MDW 2027-02-08 13:15:00 → BOS 2027-02-08 16:20:00; nonstop; 125 minutes. Local airport times.

2027-02-05 → 2027-02-08 · $350.00

  • Delta Air Lines DL2222 / DL4677: BOS 2027-02-05 13:04:00 → MDW 2027-02-05 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2027-02-05 13:04:00 → DTW 2027-02-05 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2027-02-05 17:40:00 → MDW 2027-02-05 18:01:00.
  • Delta Air Lines DL5469 / DL2558: MDW 2027-02-08 10:24:00 → BOS 2027-02-08 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2027-02-08 10:24:00 → MSP 2027-02-08 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2027-02-08 13:09:00 → BOS 2027-02-08 17:01:00.

2027-02-05 → 2027-02-08 · $270.00

  • Southwest Airlines WN4995: BOS 2027-02-05 07:10:00 → MDW 2027-02-05 08:55:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2900: MDW 2027-02-08 13:15:00 → BOS 2027-02-08 16:20:00; nonstop; 125 minutes. Local airport times.

2027-02-05 → 2027-02-08 · $280.00

  • Southwest Airlines WN4765 / WN651: BOS 2027-02-05 14:25:00 → MDW 2027-02-05 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
    • WN4765: BOS 2027-02-05 14:25:00 → BNA 2027-02-05 16:15:00; layover at BNA: 195 minutes.
    • WN651: BNA 2027-02-05 19:30:00 → MDW 2027-02-05 21:05:00.
  • Southwest Airlines WN2900: MDW 2027-02-08 13:15:00 → BOS 2027-02-08 16:20:00; nonstop; 125 minutes. Local airport times.

2027-02-05 → 2027-02-08 · $280.00

  • Southwest Airlines WN819 / WN287: BOS 2027-02-05 05:35:00 → MDW 2027-02-05 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2027-02-05 05:35:00 → STL 2027-02-05 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2027-02-05 10:55:00 → MDW 2027-02-05 12:05:00.
  • Southwest Airlines WN2900: MDW 2027-02-08 13:15:00 → BOS 2027-02-08 16:20:00; nonstop; 125 minutes. Local airport times.

2027-02-05 → 2027-02-08 · $280.00

  • Southwest Airlines WN1426 / WN1070: BOS 2027-02-05 07:25:00 → MDW 2027-02-05 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN1426: BOS 2027-02-05 07:25:00 → BWI 2027-02-05 09:15:00; layover at BWI: 110 minutes.
    • WN1070: BWI 2027-02-05 11:05:00 → MDW 2027-02-05 12:15:00.
  • Southwest Airlines WN2900: MDW 2027-02-08 13:15:00 → BOS 2027-02-08 16:20:00; nonstop; 125 minutes. Local airport times.

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