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Chicago → Boston

Dec 21, 2026 · return Dec 28, 2026

ORD → BOS1 adulteconomyRound trip

13 flight options · 5 airlines

Nonstop flights

Mon, Dec 21 – Mon, Dec 28

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
6:00 amORD
2h 29m
Nonstop
9:29 amBOS
American Airlines
12:12 pmBOS
3h 10m
Nonstop
2:22 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
6:05 amORD
2h 18m
Nonstop
9:23 amBOS
United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Delta Air Lines
3:05 pmORD
2h 31m
Nonstop
6:36 pmBOS
Delta Air Lines
8:10 pmBOS
2h 54m
Nonstop
10:04 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
5:17 pmORD
2h 30m
Nonstop
8:47 pmBOS
American Airlines
12:12 pmBOS
3h 10m
Nonstop
2:22 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
12:29 pmORD
2h 24m
Nonstop
3:53 pmBOS
United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Delta Air Lines
10:38 amORD
2h 37m
Nonstop
2:15 pmBOS
Delta Air Lines
8:10 pmBOS
2h 54m
Nonstop
10:04 pmORD

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Mon, Dec 28

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
8:00 amORD
5h 17m
ROC · 1h 54m
2:17 pmBOS
American Airlines
12:12 pmBOS
3h 10m
Nonstop
2:22 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
8:00 amORD
5h 9m
BUF · 1h 45m
2:09 pmBOS
American Airlines
12:12 pmBOS
3h 10m
Nonstop
2:22 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

American Airlines
3:19 pmORD
5h
PHL · 1h 25m
9:19 pmBOS
American Airlines
12:12 pmBOS
3h 10m
Nonstop
2:22 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

Delta Air Lines
10:06 amORD
5h 19m
LGA · 1h 42m
4:25 pmBOS
Delta Air Lines
8:10 pmBOS
2h 54m
Nonstop
10:04 pmORD

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Dec 28

United Airlines
1:00 pmORD
4h 57m
IAD · 1h 12m
6:57 pmBOS
United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD

Round-trip total · 1 adult · Taxes included

Make this trip yours

ORD ⇄ BOS

Economy

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

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Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

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 → 2026-12-28JetBlue AirwaysB61012 / B6611$344.502026-10-29T01:52:47Z
2026-12-21 → 2026-12-28American AirlinesAA1951 / AA1500$377.002026-10-29T01:52:47Z
2026-12-21 → 2026-12-28United AirlinesUA1186 / UA1414$390.002026-10-29T01:52:47Z
2026-12-21 → 2026-12-28Delta Air LinesDL2816 / DL5606$390.002026-10-29T01:52:47Z
2026-12-21 → 2026-12-28Air CanadaAC508 + AC772 / AC8695 + AC511$546.002026-10-29T01:52:47Z
2026-12-21 → 2026-12-28American AirlinesAA2332 / AA1500$377.002026-10-29T01:52:47Z
2026-12-21 → 2026-12-28United AirlinesUA1896 / UA1414$390.002026-10-29T01:52:47Z
2026-12-21 → 2026-12-28Delta Air LinesDL2570 / DL5606$390.002026-10-29T01:52:47Z
2026-12-21 → 2026-12-28American AirlinesAA3437 + AA4533 / AA1500$367.252026-10-29T01:52:47Z
2026-12-21 → 2026-12-28American AirlinesAA4780 + AA4026 / AA1500$367.252026-10-29T01:52:47Z
2026-12-21 → 2026-12-28American AirlinesAA2840 + AA1776 / AA1500$367.252026-10-29T01:52:47Z
2026-12-21 → 2026-12-28Delta Air LinesDL2917 + DL5727 / DL5606$380.252026-10-29T01:52:47Z
2026-12-21 → 2026-12-28United AirlinesUA1128 + UA688 / UA1414$380.252026-10-29T01:52:47Z

2026-12-21 → 2026-12-28 · $344.50

  • JetBlue Airways B61012: ORD 2026-12-21 17:46:00 → BOS 2026-12-21 21:14:00; nonstop; 148 minutes. Local airport times.
  • JetBlue Airways B6611: BOS 2026-12-28 14:40:00 → ORD 2026-12-28 16:40:00; nonstop; 180 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $377.00

  • American Airlines AA1951: ORD 2026-12-21 06:00:00 → BOS 2026-12-21 09:29:00; nonstop; 149 minutes. Local airport times.
  • American Airlines AA1500: BOS 2026-12-28 12:12:00 → ORD 2026-12-28 14:22:00; nonstop; 190 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $390.00

  • United Airlines UA1186: ORD 2026-12-21 06:05:00 → BOS 2026-12-21 09:23:00; nonstop; 138 minutes. Local airport times.
  • United Airlines UA1414: BOS 2026-12-28 06:00:00 → ORD 2026-12-28 08:00:00; nonstop; 180 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $390.00

  • Delta Air Lines DL2816: ORD 2026-12-21 15:05:00 → BOS 2026-12-21 18:36:00; nonstop; 151 minutes. Local airport times.
  • Delta Air Lines DL5606: BOS 2026-12-28 20:10:00 → ORD 2026-12-28 22:04:00; nonstop; 174 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $546.00

  • Air Canada AC508 / AC772: ORD 2026-12-21 16:30:00 → BOS 2026-12-21 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
    • AC508: ORD 2026-12-21 16:30:00 → YYZ 2026-12-21 19:10:00; layover at YYZ: 105 minutes.
    • AC772: YYZ 2026-12-21 20:55:00 → BOS 2026-12-21 22:37:00.
  • Air Canada AC8695 / AC511: BOS 2026-12-28 15:10:00 → ORD 2026-12-28 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
    • AC8695: BOS 2026-12-28 15:10:00 → YYZ 2026-12-28 17:11:00; layover at YYZ: 104 minutes.
    • AC511: YYZ 2026-12-28 18:55:00 → ORD 2026-12-28 19:58:00.

2026-12-21 → 2026-12-28 · $377.00

  • American Airlines AA2332: ORD 2026-12-21 17:17:00 → BOS 2026-12-21 20:47:00; nonstop; 150 minutes. Local airport times.
  • American Airlines AA1500: BOS 2026-12-28 12:12:00 → ORD 2026-12-28 14:22:00; nonstop; 190 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $390.00

  • United Airlines UA1896: ORD 2026-12-21 12:29:00 → BOS 2026-12-21 15:53:00; nonstop; 144 minutes. Local airport times.
  • United Airlines UA1414: BOS 2026-12-28 06:00:00 → ORD 2026-12-28 08:00:00; nonstop; 180 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $390.00

  • Delta Air Lines DL2570: ORD 2026-12-21 10:38:00 → BOS 2026-12-21 14:15:00; nonstop; 157 minutes. Local airport times.
  • Delta Air Lines DL5606: BOS 2026-12-28 20:10:00 → ORD 2026-12-28 22:04:00; nonstop; 174 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $367.25

  • American Airlines AA3437 / AA4533: ORD 2026-12-21 08:00:00 → BOS 2026-12-21 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
    • AA3437: ORD 2026-12-21 08:00:00 → ROC 2026-12-21 10:56:00; layover at ROC: 114 minutes.
    • AA4533: ROC 2026-12-21 12:50:00 → BOS 2026-12-21 14:17:00.
  • American Airlines AA1500: BOS 2026-12-28 12:12:00 → ORD 2026-12-28 14:22:00; nonstop; 190 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $367.25

  • American Airlines AA4780 / AA4026: ORD 2026-12-21 08:00:00 → BOS 2026-12-21 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
    • AA4780: ORD 2026-12-21 08:00:00 → BUF 2026-12-21 10:45:00; layover at BUF: 105 minutes.
    • AA4026: BUF 2026-12-21 12:30:00 → BOS 2026-12-21 14:09:00.
  • American Airlines AA1500: BOS 2026-12-28 12:12:00 → ORD 2026-12-28 14:22:00; nonstop; 190 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $367.25

  • American Airlines AA2840 / AA1776: ORD 2026-12-21 15:19:00 → BOS 2026-12-21 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
    • AA2840: ORD 2026-12-21 15:19:00 → PHL 2026-12-21 18:30:00; layover at PHL: 85 minutes.
    • AA1776: PHL 2026-12-21 19:55:00 → BOS 2026-12-21 21:19:00.
  • American Airlines AA1500: BOS 2026-12-28 12:12:00 → ORD 2026-12-28 14:22:00; nonstop; 190 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $380.25

  • Delta Air Lines DL2917 / DL5727: ORD 2026-12-21 10:06:00 → BOS 2026-12-21 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
    • DL2917: ORD 2026-12-21 10:06:00 → LGA 2026-12-21 13:18:00; layover at LGA: 102 minutes.
    • DL5727: LGA 2026-12-21 15:00:00 → BOS 2026-12-21 16:25:00.
  • Delta Air Lines DL5606: BOS 2026-12-28 20:10:00 → ORD 2026-12-28 22:04:00; nonstop; 174 minutes. Local airport times.

2026-12-21 → 2026-12-28 · $380.25

  • United Airlines UA1128 / UA688: ORD 2026-12-21 13:00:00 → BOS 2026-12-21 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
    • UA1128: ORD 2026-12-21 13:00:00 → IAD 2026-12-21 16:03:00; layover at IAD: 72 minutes.
    • UA688: IAD 2026-12-21 17:15:00 → BOS 2026-12-21 18:57:00.
  • United Airlines UA1414: BOS 2026-12-28 06:00:00 → ORD 2026-12-28 08:00:00; nonstop; 180 minutes. Local airport times.

More dates for this route