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Boston → Chicago

Dec 21, 2026 · return Dec 31, 2026

BOS → ORD1 adulteconomyRound trip

14 flight options · 5 airlines

Nonstop flights

Mon, Dec 21 – Thu, Dec 31

JetBlue Airways
9:59 amBOS
3h 1m
Nonstop
12:00 pmORD
JetBlue Airways
5:46 pmORD
2h 28m
Nonstop
9:14 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

United Airlines
2:57 pmBOS
3h 2m
Nonstop
4:59 pmORD
United Airlines
10:28 amORD
2h 26m
Nonstop
1:54 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

American Airlines
10:24 amBOS
3h 11m
Nonstop
12:35 pmORD
American Airlines
12:35 pmORD
2h 32m
Nonstop
4:07 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Delta Air Lines
8:10 pmBOS
2h 54m
Nonstop
10:04 pmORD
Delta Air Lines
10:35 amORD
2h 24m
Nonstop
1:59 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

JetBlue Airways
2:40 pmBOS
3h
Nonstop
4:40 pmORD
JetBlue Airways
5:46 pmORD
2h 28m
Nonstop
9:14 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

American Airlines
12:12 pmBOS
3h 10m
Nonstop
2:22 pmORD
American Airlines
12:35 pmORD
2h 32m
Nonstop
4:07 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD
United Airlines
10:28 amORD
2h 26m
Nonstop
1:54 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Delta Air Lines
7:30 amBOS
3h 5m
Nonstop
9:35 amORD
Delta Air Lines
10:35 amORD
2h 24m
Nonstop
1:59 pmBOS

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Thu, Dec 31

Air Canada
3:10 pmBOS
5h 48m
YYZ · 1h 44m
7:58 pmORD
Air Canada
4:30 pmORD
5h 7m
YYZ · 1h 45m
10:37 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

American Airlines
10:00 amBOS
4h 59m
SYR · 1h 8m
1:59 pmORD
American Airlines
12:35 pmORD
2h 32m
Nonstop
4:07 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

American Airlines
3:45 pmBOS
5h 45m
PHL · 1h 5m
8:30 pmORD
American Airlines
12:35 pmORD
2h 32m
Nonstop
4:07 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

American Airlines
10:07 amBOS
6h 7m
CVG · 1h 44m
3:14 pmORD
American Airlines
12:35 pmORD
2h 32m
Nonstop
4:07 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

United Airlines
2:40 pmBOS
5h 25m
IAD · 1h 12m
7:05 pmORD
United Airlines
10:28 amORD
2h 26m
Nonstop
1:54 pmBOS

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

United Airlines
3:42 pmBOS
5h 24m
EWR · 1h 2m
8:06 pmORD
United Airlines
10:28 amORD
2h 26m
Nonstop
1:54 pmBOS

Round-trip total · 1 adult · Taxes included

Make this trip yours

BOS ⇄ ORD

Economy

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

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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2026-12-31JetBlue AirwaysB6111 / B61012$337.882026-10-29T00:52:35Z
2026-12-21 → 2026-12-31United AirlinesUA2496 / UA1606$369.752026-10-29T00:52:35Z
2026-12-21 → 2026-12-31American AirlinesAA2015 / AA4477$369.752026-10-29T00:52:35Z
2026-12-21 → 2026-12-31Delta Air LinesDL5606 / DL2570$382.502026-10-29T00:52:35Z
2026-12-21 → 2026-12-31Air CanadaAC8695 + AC511 / AC508 + AC772$561.002026-10-29T00:52:35Z
2026-12-21 → 2026-12-31JetBlue AirwaysB6611 / B61012$337.882026-10-29T00:52:35Z
2026-12-21 → 2026-12-31American AirlinesAA1500 / AA4477$369.752026-10-29T00:52:35Z
2026-12-21 → 2026-12-31United AirlinesUA1414 / UA1606$369.752026-10-29T00:52:35Z
2026-12-21 → 2026-12-31Delta Air LinesDL2570 / DL2570$382.502026-10-29T00:52:35Z
2026-12-21 → 2026-12-31American AirlinesAA4133 + AA4390 / AA4477$382.752026-10-29T00:52:35Z
2026-12-21 → 2026-12-31American AirlinesAA4798 + AA3177 / AA4477$382.752026-10-29T00:52:35Z
2026-12-21 → 2026-12-31American AirlinesAA4609 + AA4733 / AA4477$382.752026-10-29T00:52:35Z
2026-12-21 → 2026-12-31United AirlinesUA721 + UA2497 / UA1606$386.002026-10-29T00:52:35Z
2026-12-21 → 2026-12-31United AirlinesUA546 + UA703 / UA1606$386.002026-10-29T00:52:35Z

2026-12-21 → 2026-12-31 · $337.88

  • JetBlue Airways B6111: BOS 2026-12-21 09:59:00 → ORD 2026-12-21 12:00:00; nonstop; 181 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2026-12-31 17:46:00 → BOS 2026-12-31 21:14:00; nonstop; 148 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $369.75

  • United Airlines UA2496: BOS 2026-12-21 14:57:00 → ORD 2026-12-21 16:59:00; nonstop; 182 minutes. Local airport times.
  • United Airlines UA1606: ORD 2026-12-31 10:28:00 → BOS 2026-12-31 13:54:00; nonstop; 146 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $369.75

  • American Airlines AA2015: BOS 2026-12-21 10:24:00 → ORD 2026-12-21 12:35:00; nonstop; 191 minutes. Local airport times.
  • American Airlines AA4477: ORD 2026-12-31 12:35:00 → BOS 2026-12-31 16:07:00; nonstop; 152 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $382.50

  • Delta Air Lines DL5606: BOS 2026-12-21 20:10:00 → ORD 2026-12-21 22:04:00; nonstop; 174 minutes. Local airport times.
  • Delta Air Lines DL2570: ORD 2026-12-31 10:35:00 → BOS 2026-12-31 13:59:00; nonstop; 144 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $561.00

  • Air Canada AC8695 / AC511: BOS 2026-12-21 15:10:00 → ORD 2026-12-21 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
    • AC8695: BOS 2026-12-21 15:10:00 → YYZ 2026-12-21 17:11:00; layover at YYZ: 104 minutes.
    • AC511: YYZ 2026-12-21 18:55:00 → ORD 2026-12-21 19:58:00.
  • Air Canada AC508 / AC772: ORD 2026-12-31 16:30:00 → BOS 2026-12-31 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
    • AC508: ORD 2026-12-31 16:30:00 → YYZ 2026-12-31 19:10:00; layover at YYZ: 105 minutes.
    • AC772: YYZ 2026-12-31 20:55:00 → BOS 2026-12-31 22:37:00.

2026-12-21 → 2026-12-31 · $337.88

  • JetBlue Airways B6611: BOS 2026-12-21 14:40:00 → ORD 2026-12-21 16:40:00; nonstop; 180 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2026-12-31 17:46:00 → BOS 2026-12-31 21:14:00; nonstop; 148 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $369.75

  • American Airlines AA1500: BOS 2026-12-21 12:12:00 → ORD 2026-12-21 14:22:00; nonstop; 190 minutes. Local airport times.
  • American Airlines AA4477: ORD 2026-12-31 12:35:00 → BOS 2026-12-31 16:07:00; nonstop; 152 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $369.75

  • United Airlines UA1414: BOS 2026-12-21 06:00:00 → ORD 2026-12-21 08:00:00; nonstop; 180 minutes. Local airport times.
  • United Airlines UA1606: ORD 2026-12-31 10:28:00 → BOS 2026-12-31 13:54:00; nonstop; 146 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $382.50

  • Delta Air Lines DL2570: BOS 2026-12-21 07:30:00 → ORD 2026-12-21 09:35:00; nonstop; 185 minutes. Local airport times.
  • Delta Air Lines DL2570: ORD 2026-12-31 10:35:00 → BOS 2026-12-31 13:59:00; nonstop; 144 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $382.75

  • American Airlines AA4133 / AA4390: BOS 2026-12-21 10:00:00 → ORD 2026-12-21 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
    • AA4133: BOS 2026-12-21 10:00:00 → SYR 2026-12-21 11:23:00; layover at SYR: 68 minutes.
    • AA4390: SYR 2026-12-21 12:31:00 → ORD 2026-12-21 13:59:00.
  • American Airlines AA4477: ORD 2026-12-31 12:35:00 → BOS 2026-12-31 16:07:00; nonstop; 152 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $382.75

  • American Airlines AA4798 / AA3177: BOS 2026-12-21 15:45:00 → ORD 2026-12-21 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
    • AA4798: BOS 2026-12-21 15:45:00 → PHL 2026-12-21 17:30:00; layover at PHL: 65 minutes.
    • AA3177: PHL 2026-12-21 18:35:00 → ORD 2026-12-21 20:30:00.
  • American Airlines AA4477: ORD 2026-12-31 12:35:00 → BOS 2026-12-31 16:07:00; nonstop; 152 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $382.75

  • American Airlines AA4609 / AA4733: BOS 2026-12-21 10:07:00 → ORD 2026-12-21 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
    • AA4609: BOS 2026-12-21 10:07:00 → CVG 2026-12-21 12:50:00; layover at CVG: 104 minutes.
    • AA4733: CVG 2026-12-21 14:34:00 → ORD 2026-12-21 15:14:00.
  • American Airlines AA4477: ORD 2026-12-31 12:35:00 → BOS 2026-12-31 16:07:00; nonstop; 152 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $386.00

  • United Airlines UA721 / UA2497: BOS 2026-12-21 14:40:00 → ORD 2026-12-21 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
    • UA721: BOS 2026-12-21 14:40:00 → IAD 2026-12-21 16:27:00; layover at IAD: 72 minutes.
    • UA2497: IAD 2026-12-21 17:39:00 → ORD 2026-12-21 19:05:00.
  • United Airlines UA1606: ORD 2026-12-31 10:28:00 → BOS 2026-12-31 13:54:00; nonstop; 146 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $386.00

  • United Airlines UA546 / UA703: BOS 2026-12-21 15:42:00 → ORD 2026-12-21 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
    • UA546: BOS 2026-12-21 15:42:00 → EWR 2026-12-21 17:08:00; layover at EWR: 62 minutes.
    • UA703: EWR 2026-12-21 18:10:00 → ORD 2026-12-21 20:06:00.
  • United Airlines UA1606: ORD 2026-12-31 10:28:00 → BOS 2026-12-31 13:54:00; nonstop; 146 minutes. Local airport times.

More dates for this route