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Route overview: Boston to Chicago (MDW) flight deals

Boston → Chicago

Dec 15, 2026 · return Dec 29, 2026

BOS → MDW1 adulteconomyRound trip

7 flight options · 3 airlines

Nonstop flights

Tue, Dec 15 – Tue, Dec 29

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

Round-trip total · 1 adult · Taxes included

Tue, Dec 15 – Tue, Dec 29

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

Tue, Dec 15 – Tue, Dec 29

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

Tue, Dec 15 – Tue, Dec 29

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

Tue, Dec 15 – Tue, Dec 29

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

Tue, Dec 15 – Tue, Dec 29

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

Tue, Dec 15 – Tue, Dec 29

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 routeDec 14, 2026 → Dec 28, 2026Dec 16, 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.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Boston to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-15 → 2026-12-29Southwest AirlinesWN816 / WN2900$303.752026-10-29T00:52:27Z
2026-12-15 → 2026-12-29Frontier Airlines / Southwest AirlinesF93511 + F92779 / WN2900$258.752026-10-29T00:52:27Z
2026-12-15 → 2026-12-29Delta Air LinesDL2222 + DL4677 / DL5469 + DL2558$393.752026-10-29T00:52:27Z
2026-12-15 → 2026-12-29Southwest AirlinesWN4995 / WN2900$303.752026-10-29T00:52:27Z
2026-12-15 → 2026-12-29Southwest AirlinesWN4765 + WN651 / WN2900$313.752026-10-29T00:52:27Z
2026-12-15 → 2026-12-29Southwest AirlinesWN819 + WN287 / WN2900$313.752026-10-29T00:52:27Z
2026-12-15 → 2026-12-29Southwest AirlinesWN1426 + WN1070 / WN2900$313.752026-10-29T00:52:27Z

2026-12-15 → 2026-12-29 · $303.75

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

2026-12-15 → 2026-12-29 · $258.75

  • Frontier Airlines F93511 / F92779: BOS 2026-12-15 12:15:00 → MDW 2026-12-15 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
    • F93511: BOS 2026-12-15 12:15:00 → ATL 2026-12-15 15:36:00; layover at ATL: 69 minutes.
    • F92779: ATL 2026-12-15 16:45:00 → MDW 2026-12-15 17:47:00.
  • Southwest Airlines WN2900: MDW 2026-12-29 13:15:00 → BOS 2026-12-29 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-15 → 2026-12-29 · $393.75

  • 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.
  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-29 10:24:00 → BOS 2026-12-29 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-29 10:24:00 → MSP 2026-12-29 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-29 13:09:00 → BOS 2026-12-29 17:01:00.

2026-12-15 → 2026-12-29 · $303.75

  • Southwest Airlines WN4995: BOS 2026-12-15 07:10:00 → MDW 2026-12-15 08:55:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2900: MDW 2026-12-29 13:15:00 → BOS 2026-12-29 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-15 → 2026-12-29 · $313.75

  • Southwest Airlines WN4765 / WN651: BOS 2026-12-15 14:25:00 → MDW 2026-12-15 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
    • WN4765: BOS 2026-12-15 14:25:00 → BNA 2026-12-15 16:15:00; layover at BNA: 195 minutes.
    • WN651: BNA 2026-12-15 19:30:00 → MDW 2026-12-15 21:05:00.
  • Southwest Airlines WN2900: MDW 2026-12-29 13:15:00 → BOS 2026-12-29 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-15 → 2026-12-29 · $313.75

  • Southwest Airlines WN819 / WN287: BOS 2026-12-15 05:35:00 → MDW 2026-12-15 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-12-15 05:35:00 → STL 2026-12-15 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-12-15 10:55:00 → MDW 2026-12-15 12:05:00.
  • Southwest Airlines WN2900: MDW 2026-12-29 13:15:00 → BOS 2026-12-29 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-15 → 2026-12-29 · $313.75

  • Southwest Airlines WN1426 / WN1070: BOS 2026-12-15 07:25:00 → MDW 2026-12-15 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN1426: BOS 2026-12-15 07:25:00 → BWI 2026-12-15 09:15:00; layover at BWI: 110 minutes.
    • WN1070: BWI 2026-12-15 11:05:00 → MDW 2026-12-15 12:15:00.
  • Southwest Airlines WN2900: MDW 2026-12-29 13:15:00 → BOS 2026-12-29 16:20:00; nonstop; 125 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Boston (BOS) to Chicago (MDW) · Dec 15, 2026 · return Dec 29, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
  • 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 Boston to Chicago (MDW) 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.