Chicago (MDW) to Boston (BOS), Nov 24, 2026: round trips from $333, one way from $209

Chicago (MDW) to Boston (BOS), Nov 24, 2026: round trips from $333, one way from $209 on Axel, checked Nov 13, 2026. Lowest published fares: $333 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 24, 2026 – Dec 2, 2026; $209 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 24, 2026; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Exact travel dates Airline Flights Times, duration, stops Total price Price checked
2026-11-24 · one way Southwest Airlines WN4113 07:45:00→11:00:00 2h 15m nonstop Axel-exclusive $209 Nov 13, 2026
2026-11-24 · one way Delta Air Lines DL4688 + DL1707 13:31:00→20:51:00 6h 20m 1 stop via DTW Axel-exclusive $277 Nov 13, 2026
2026-11-24 → 2026-11-25 Southwest Airlines WN4113 / WN819 + WN287 07:45:00→11:00:00 2h 15m nonstop · 05:35:00→12:05:00 7h 30m 1 stop via STL Axel-exclusive $381 Nov 13, 2026
2026-11-24 → 2026-11-25 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $527 Nov 13, 2026
2026-11-24 → 2026-11-26 Southwest Airlines WN4113 / WN2939 07:45:00→11:00:00 2h 15m nonstop · 12:20:00→14:05:00 2h 45m nonstop Axel-exclusive $392 Nov 13, 2026
2026-11-24 → 2026-11-26 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $527 Nov 13, 2026
2026-11-24 → 2026-11-27 Southwest Airlines WN4113 / WN816 07:45:00→11:00:00 2h 15m nonstop · 18:30:00→20:15:00 2h 45m nonstop Axel-exclusive $392 Nov 13, 2026
2026-11-24 → 2026-11-27 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $527 Nov 13, 2026
2026-11-24 → 2026-11-28 Southwest Airlines WN4113 / WN2939 07:45:00→11:00:00 2h 15m nonstop · 12:20:00→14:05:00 2h 45m nonstop Axel-exclusive $392 Nov 13, 2026
2026-11-24 → 2026-11-28 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $527 Nov 13, 2026
2026-11-24 → 2026-11-29 Southwest Airlines WN4113 / WN2972 07:45:00→11:00:00 2h 15m nonstop · 06:45:00→08:30:00 2h 45m nonstop Axel-exclusive $392 Nov 13, 2026
2026-11-24 → 2026-11-29 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $527 Nov 13, 2026
2026-11-24 → 2026-11-30 Southwest Airlines WN4113 / WN816 07:45:00→11:00:00 2h 15m nonstop · 18:30:00→20:15:00 2h 45m nonstop Axel-exclusive $392 Nov 13, 2026
2026-11-24 → 2026-11-30 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $527 Nov 13, 2026
2026-11-24 → 2026-12-01 Southwest Airlines WN4113 / WN816 07:45:00→11:00:00 2h 15m nonstop · 17:55:00→19:40:00 2h 45m nonstop Axel-exclusive $341 Nov 13, 2026
2026-11-24 → 2026-12-01 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $458 Nov 13, 2026
2026-11-24 → 2026-12-02 Southwest Airlines WN4113 / WN819 + WN287 07:45:00→11:00:00 2h 15m nonstop · 05:35:00→12:05:00 7h 30m 1 stop via STL Axel-exclusive $333 Nov 13, 2026
2026-11-24 → 2026-12-02 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $458 Nov 13, 2026
2026-11-24 → 2026-12-03 Southwest Airlines WN4113 / WN816 07:45:00→11:00:00 2h 15m nonstop · 18:30:00→20:15:00 2h 45m nonstop Axel-exclusive $341 Nov 13, 2026
2026-11-24 → 2026-12-03 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $458 Nov 13, 2026
2026-11-24 → 2026-12-04 Southwest Airlines WN4113 / WN816 07:45:00→11:00:00 2h 15m nonstop · 18:30:00→20:15:00 2h 45m nonstop Axel-exclusive $341 Nov 13, 2026
2026-11-24 → 2026-12-04 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $458 Nov 13, 2026
2026-11-24 → 2026-12-05 Southwest Airlines WN4113 / WN2939 07:45:00→11:00:00 2h 15m nonstop · 12:20:00→14:05:00 2h 45m nonstop Axel-exclusive $341 Nov 13, 2026
2026-11-24 → 2026-12-05 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $458 Nov 13, 2026
2026-11-24 → 2026-12-06 Southwest Airlines WN4113 / WN816 07:45:00→11:00:00 2h 15m nonstop · 18:30:00→20:15:00 2h 45m nonstop Axel-exclusive $341 Nov 13, 2026
2026-11-24 → 2026-12-06 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $458 Nov 13, 2026
2026-11-24 → 2026-12-07 Southwest Airlines WN4113 / WN816 07:45:00→11:00:00 2h 15m nonstop · 18:30:00→20:15:00 2h 45m nonstop Axel-exclusive $341 Nov 13, 2026
2026-11-24 → 2026-12-07 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $458 Nov 13, 2026
2026-11-24 → 2026-12-08 Southwest Airlines WN4113 / WN816 07:45:00→11:00:00 2h 15m nonstop · 17:55:00→19:40:00 2h 45m nonstop Axel-exclusive $341 Nov 13, 2026
2026-11-24 → 2026-12-08 Delta Air Lines DL4688 + DL1707 / DL2222 + DL4677 13:31:00→20:51:00 6h 20m 1 stop via DTW · 13:04:00→18:01:00 5h 57m 1 stop via DTW Axel-exclusive $458 Nov 13, 2026

Hotels in Boston for these trips

Hotels: under a trip, hotels in Boston for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2026-11-24 · one way · Axel-exclusive $209

2026-11-24 · one way · Axel-exclusive $277

2026-11-24 → 2026-11-25 · Axel-exclusive $381

2026-11-24 → 2026-11-25 · Axel-exclusive $527

2026-11-24 → 2026-11-26 · Axel-exclusive $392

2026-11-24 → 2026-11-26 · Axel-exclusive $527

2026-11-24 → 2026-11-27 · Axel-exclusive $392

2026-11-24 → 2026-11-27 · Axel-exclusive $527

2026-11-24 → 2026-11-28 · Axel-exclusive $392

2026-11-24 → 2026-11-28 · Axel-exclusive $527

2026-11-24 → 2026-11-30 · Axel-exclusive $392

2026-11-24 → 2026-11-30 · Axel-exclusive $527

2026-11-24 → 2026-12-01 · Axel-exclusive $341

2026-11-24 → 2026-12-01 · Axel-exclusive $458

2026-11-24 → 2026-12-02 · Axel-exclusive $333

2026-11-24 → 2026-12-02 · Axel-exclusive $458

2026-11-24 → 2026-12-04 · Axel-exclusive $341

2026-11-24 → 2026-12-04 · Axel-exclusive $458

2026-11-24 → 2026-12-05 · Axel-exclusive $341

2026-11-24 → 2026-12-05 · Axel-exclusive $458

2026-11-24 → 2026-12-06 · Axel-exclusive $341

2026-11-24 → 2026-12-06 · Axel-exclusive $458

2026-11-24 → 2026-12-08 · Axel-exclusive $341

2026-11-24 → 2026-12-08 · Axel-exclusive $458

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