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Route overview: Boston to Chicago (MDW) flight deals

Boston → Chicago

Jan 21, 2027 · return Jan 28, 2027

BOS → MDW1 adulteconomyRound trip

7 flight options · 3 airlines

Nonstop flights

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
7:05 amBOS
2h 45m
Nonstop
8:50 amMDW
Southwest Airlines
7:35 pmMDW
2h 20m
Nonstop
10:55 pmBOS

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
5:55 pmBOS
2h 45m
Nonstop
7:40 pmMDW
Southwest Airlines
7:35 pmMDW
2h 20m
Nonstop
10:55 pmBOS

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 – Thu, Jan 28

Frontier Airlines
12:15 pmBOS
6h 32m
ATL · 1h 9m
5:47 pmMDW
Southwest Airlines
7:35 pmMDW
2h 20m
Nonstop
10:55 pmBOS

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

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

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
5:35 amBOS
7h 30m
STL · 3h 15m
12:05 pmMDW
Southwest Airlines
7:35 pmMDW
2h 20m
Nonstop
10:55 pmBOS

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
2:25 pmBOS
7h 40m
BNA · 3h 15m
9:05 pmMDW
Southwest Airlines
7:35 pmMDW
2h 20m
Nonstop
10:55 pmBOS

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Jan 28

Southwest Airlines
7:25 amBOS
5h 50m
BWI · 1h 50m
12:15 pmMDW
Southwest Airlines
7:35 pmMDW
2h 20m
Nonstop
10:55 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 routeJan 20, 2027 → Jan 27, 2027Jan 22, 2027 → Jan 29, 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.

Live price for these dates: opening any fare on this page checks it live and shows the current bookable total for 1 adult. Check live prices for Boston (BOS) to Chicago (MDW), Jan 21, 2027 · return Jan 28, 2027

Route overview: Boston to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-21 → 2027-01-28Southwest AirlinesWN2185 / WN2902$270.002026-10-29T00:52:27Z
2027-01-21 → 2027-01-28Frontier Airlines / Southwest AirlinesF93511 + F92779 / WN2902$225.002026-10-29T00:52:27Z
2027-01-21 → 2027-01-28Delta Air LinesDL2222 + DL4677 / DL5469 + DL2558$350.002026-10-29T00:52:27Z
2027-01-21 → 2027-01-28Southwest AirlinesWN816 / WN2902$270.002026-10-29T00:52:27Z
2027-01-21 → 2027-01-28Southwest AirlinesWN819 + WN287 / WN2902$280.002026-10-29T00:52:27Z
2027-01-21 → 2027-01-28Southwest AirlinesWN4765 + WN651 / WN2902$280.002026-10-29T00:52:27Z
2027-01-21 → 2027-01-28Southwest AirlinesWN1426 + WN1070 / WN2902$280.002026-10-29T00:52:27Z

2027-01-21 → 2027-01-28 · $270.00

  • Southwest Airlines WN2185: BOS 2027-01-21 07:05:00 → MDW 2027-01-21 08:50:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2902: MDW 2027-01-28 19:35:00 → BOS 2027-01-28 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $225.00

  • Frontier Airlines F93511 / F92779: BOS 2027-01-21 12:15:00 → MDW 2027-01-21 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
    • F93511: BOS 2027-01-21 12:15:00 → ATL 2027-01-21 15:36:00; layover at ATL: 69 minutes.
    • F92779: ATL 2027-01-21 16:45:00 → MDW 2027-01-21 17:47:00.
  • Southwest Airlines WN2902: MDW 2027-01-28 19:35:00 → BOS 2027-01-28 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $350.00

  • Delta Air Lines DL2222 / DL4677: BOS 2027-01-21 13:04:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2027-01-21 13:04:00 → DTW 2027-01-21 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
  • Delta Air Lines DL5469 / DL2558: MDW 2027-01-28 10:24:00 → BOS 2027-01-28 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2027-01-28 10:24:00 → MSP 2027-01-28 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2027-01-28 13:09:00 → BOS 2027-01-28 17:01:00.

2027-01-21 → 2027-01-28 · $270.00

  • Southwest Airlines WN816: BOS 2027-01-21 17:55:00 → MDW 2027-01-21 19:40:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2902: MDW 2027-01-28 19:35:00 → BOS 2027-01-28 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $280.00

  • Southwest Airlines WN819 / WN287: BOS 2027-01-21 05:35:00 → MDW 2027-01-21 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2027-01-21 05:35:00 → STL 2027-01-21 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2027-01-21 10:55:00 → MDW 2027-01-21 12:05:00.
  • Southwest Airlines WN2902: MDW 2027-01-28 19:35:00 → BOS 2027-01-28 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $280.00

  • Southwest Airlines WN4765 / WN651: BOS 2027-01-21 14:25:00 → MDW 2027-01-21 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
    • WN4765: BOS 2027-01-21 14:25:00 → BNA 2027-01-21 16:15:00; layover at BNA: 195 minutes.
    • WN651: BNA 2027-01-21 19:30:00 → MDW 2027-01-21 21:05:00.
  • Southwest Airlines WN2902: MDW 2027-01-28 19:35:00 → BOS 2027-01-28 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-21 → 2027-01-28 · $280.00

  • Southwest Airlines WN1426 / WN1070: BOS 2027-01-21 07:25:00 → MDW 2027-01-21 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN1426: BOS 2027-01-21 07:25:00 → BWI 2027-01-21 09:15:00; layover at BWI: 110 minutes.
    • WN1070: BWI 2027-01-21 11:05:00 → MDW 2027-01-21 12:15:00.
  • Southwest Airlines WN2902: MDW 2027-01-28 19:35:00 → BOS 2027-01-28 22:55:00; nonstop; 140 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Boston (BOS) to Chicago (MDW) · Jan 21, 2027 · return Jan 28, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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  • 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 Boston to Chicago (MDW) flight deals · Flight search guide.
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