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Route overview: Chicago to Boston (BOS) flight deals

Chicago → Boston

Dec 28, 2026 · return Dec 29, 2026

MDW → BOS1 adulteconomyRound trip

7 flight options · 2 airlines

Nonstop flights

Mon, Dec 28 – Tue, Dec 29

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

Mon, Dec 28 – Tue, Dec 29

Southwest Airlines
8:40 pmMDW
2h 15m
Nonstop
11:55 pmBOS
Southwest Airlines
5:55 pmBOS
2h 45m
Nonstop
7:40 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 28 – Tue, Dec 29

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

Mon, Dec 28 – Tue, Dec 29

Southwest Airlines
1:40 pmMDW
7h 5m
STL · 3h 15m
9:45 pmBOS
Southwest Airlines
5:55 pmBOS
2h 45m
Nonstop
7:40 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 28 – Tue, Dec 29

Southwest Airlines
5:25 pmMDW
6h 15m
BNA · 2h 20m
12:40 am+1BOS
Southwest Airlines
5:55 pmBOS
2h 45m
Nonstop
7:40 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 28 – Tue, Dec 29

Southwest Airlines
2:30 pmMDW
5h 50m
BWI · 2h 30m
9:20 pmBOS
Southwest Airlines
5:55 pmBOS
2h 45m
Nonstop
7:40 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 28 – Tue, Dec 29

Delta Air Lines
1:31 pmMDW
6h 20m
DTW · 3h 8m
8:51 pmBOS
Delta Air Lines
1:04 pmBOS
5h 57m
DTW · 2h 21m
6:01 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ BOS

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 routeDec 27, 2026 → Dec 28, 2026Dec 29, 2026 → Dec 30, 2026
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: Chicago to Boston (BOS) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-28 → 2026-12-29Southwest AirlinesWN2900 / WN816$362.502026-10-29T01:29:04Z
2026-12-28 → 2026-12-29Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677$487.502026-10-29T01:29:04Z
2026-12-28 → 2026-12-29Southwest AirlinesWN249 / WN816$362.502026-10-29T01:29:04Z
2026-12-28 → 2026-12-29Southwest AirlinesWN3092 + WN4431 / WN816$353.132026-10-29T01:29:04Z
2026-12-28 → 2026-12-29Southwest AirlinesWN2897 + WN497 / WN816$353.132026-10-29T01:29:04Z
2026-12-28 → 2026-12-29Southwest AirlinesWN14 + WN4024 / WN816$353.132026-10-29T01:29:04Z
2026-12-28 → 2026-12-29Delta Air LinesDL4688 + DL1707 / DL2222 + DL4677$487.502026-10-29T01:29:04Z

2026-12-28 → 2026-12-29 · $362.50

  • Southwest Airlines WN2900: MDW 2026-12-28 13:15:00 → BOS 2026-12-28 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN816: BOS 2026-12-29 17:55:00 → MDW 2026-12-29 19:40:00; nonstop; 165 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $487.50

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-28 10:24:00 → BOS 2026-12-28 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-28 10:24:00 → MSP 2026-12-28 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-28 13:09:00 → BOS 2026-12-28 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-29 13:04:00 → MDW 2026-12-29 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-29 13:04:00 → DTW 2026-12-29 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-29 17:40:00 → MDW 2026-12-29 18:01:00.

2026-12-28 → 2026-12-29 · $362.50

  • Southwest Airlines WN249: MDW 2026-12-28 20:40:00 → BOS 2026-12-28 23:55:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN816: BOS 2026-12-29 17:55:00 → MDW 2026-12-29 19:40:00; nonstop; 165 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $353.13

  • Southwest Airlines WN3092 / WN4431: MDW 2026-12-28 13:40:00 → BOS 2026-12-28 21:45:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN3092: MDW 2026-12-28 13:40:00 → STL 2026-12-28 14:55:00; layover at STL: 195 minutes.
    • WN4431: STL 2026-12-28 18:10:00 → BOS 2026-12-28 21:45:00.
  • Southwest Airlines WN816: BOS 2026-12-29 17:55:00 → MDW 2026-12-29 19:40:00; nonstop; 165 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $353.13

  • Southwest Airlines WN2897 / WN497: MDW 2026-12-28 17:25:00 → BOS 2026-12-29 00:40:00; 1 stop(s) via BNA; 375 minutes. Local airport times.
    • WN2897: MDW 2026-12-28 17:25:00 → BNA 2026-12-28 18:50:00; layover at BNA: 140 minutes.
    • WN497: BNA 2026-12-28 21:10:00 → BOS 2026-12-29 00:40:00.
  • Southwest Airlines WN816: BOS 2026-12-29 17:55:00 → MDW 2026-12-29 19:40:00; nonstop; 165 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $353.13

  • Southwest Airlines WN14 / WN4024: MDW 2026-12-28 14:30:00 → BOS 2026-12-28 21:20:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN14: MDW 2026-12-28 14:30:00 → BWI 2026-12-28 17:15:00; layover at BWI: 150 minutes.
    • WN4024: BWI 2026-12-28 19:45:00 → BOS 2026-12-28 21:20:00.
  • Southwest Airlines WN816: BOS 2026-12-29 17:55:00 → MDW 2026-12-29 19:40:00; nonstop; 165 minutes. Local airport times.

2026-12-28 → 2026-12-29 · $487.50

  • Delta Air Lines DL4688 / DL1707: MDW 2026-12-28 13:31:00 → BOS 2026-12-28 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
    • DL4688: MDW 2026-12-28 13:31:00 → DTW 2026-12-28 15:44:00; layover at DTW: 188 minutes.
    • DL1707: DTW 2026-12-28 18:52:00 → BOS 2026-12-28 20:51:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-29 13:04:00 → MDW 2026-12-29 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-29 13:04:00 → DTW 2026-12-29 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-29 17:40:00 → MDW 2026-12-29 18:01:00.

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