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Boston → Chicago

Dec 2, 2026 · return Dec 8, 2026

BOS → ORD1 adulteconomyRound trip

14 flight options · 4 airlines

Nonstop flights

Wed, Dec 2 – Tue, Dec 8

JetBlue Airways
2:40 pmBOS
3h
Nonstop
4:40 pmORD
JetBlue Airways
1:00 pmORD
2h 49m
Nonstop
4:49 pmBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

American Airlines
5:53 amBOS
3h 11m
Nonstop
8:04 amORD
American Airlines
7:13 pmORD
2h 29m
Nonstop
10:42 pmBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD
United Airlines
6:00 amORD
2h 19m
Nonstop
9:19 amBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

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

Wed, Dec 2 – Tue, Dec 8

JetBlue Airways
9:59 amBOS
3h 1m
Nonstop
12:00 pmORD
JetBlue Airways
1:00 pmORD
2h 49m
Nonstop
4:49 pmBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

American Airlines
5:58 pmBOS
3h 14m
Nonstop
8:12 pmORD
American Airlines
7:13 pmORD
2h 29m
Nonstop
10:42 pmBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

United Airlines
5:45 amBOS
3h 6m
Nonstop
7:51 amORD
United Airlines
7:00 amORD
2h 19m
Nonstop
10:19 amBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

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

Wed, Dec 2 – Tue, Dec 8

American Airlines
3:45 pmBOS
5h 45m
PHL · 1h 5m
8:30 pmORD
American Airlines
7:13 pmORD
2h 29m
Nonstop
10:42 pmBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

American Airlines
10:07 amBOS
6h 7m
CVG · 1h 44m
3:14 pmORD
American Airlines
7:13 pmORD
2h 29m
Nonstop
10:42 pmBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

American Airlines
10:00 amBOS
4h 59m
SYR · 1h 8m
1:59 pmORD
American Airlines
7:13 pmORD
2h 29m
Nonstop
10:42 pmBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

United Airlines
3:42 pmBOS
5h 24m
EWR · 1h 2m
8:06 pmORD
United Airlines
6:00 amORD
2h 19m
Nonstop
9:19 amBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

United Airlines
2:40 pmBOS
5h 25m
IAD · 1h 12m
7:05 pmORD
United Airlines
6:00 amORD
2h 19m
Nonstop
9:19 amBOS

Round-trip total · 1 adult · Taxes included

Wed, Dec 2 – Tue, Dec 8

Delta Air Lines
7:30 amBOS
3h 8m
Nonstop
9:38 amORD
Delta Air Lines
10:06 amORD
5h 19m
LGA · 1h 42m
4:25 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)
2026-12-02 → 2026-12-08JetBlue AirwaysB6611 / B6112$265.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08American AirlinesAA1379 / AA1212$290.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08United AirlinesUA1414 / UA1186$290.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08Delta Air LinesDL5606 / DL2570$300.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08JetBlue AirwaysB6111 / B6112$265.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08American AirlinesAA2461 / AA1212$290.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08United AirlinesUA1414 / UA2213$290.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08Delta Air LinesDL2570 / DL2570$300.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08American AirlinesAA4798 + AA3177 / AA1212$300.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08American AirlinesAA4609 + AA4733 / AA1212$300.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08American AirlinesAA4133 + AA4390 / AA1212$300.002026-10-29T00:52:35Z
2026-12-02 → 2026-12-08United AirlinesUA546 + UA703 / UA1186$302.502026-10-29T00:52:35Z
2026-12-02 → 2026-12-08United AirlinesUA721 + UA2497 / UA1186$302.502026-10-29T00:52:35Z
2026-12-02 → 2026-12-08Delta Air LinesDL2570 / DL2917 + DL5727$312.502026-10-29T00:52:35Z

2026-12-02 → 2026-12-08 · $265.00

  • JetBlue Airways B6611: BOS 2026-12-02 14:40:00 → ORD 2026-12-02 16:40:00; nonstop; 180 minutes. Local airport times.
  • JetBlue Airways B6112: ORD 2026-12-08 13:00:00 → BOS 2026-12-08 16:49:00; nonstop; 169 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $290.00

  • American Airlines AA1379: BOS 2026-12-02 05:53:00 → ORD 2026-12-02 08:04:00; nonstop; 191 minutes. Local airport times.
  • American Airlines AA1212: ORD 2026-12-08 19:13:00 → BOS 2026-12-08 22:42:00; nonstop; 149 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $290.00

  • United Airlines UA1414: BOS 2026-12-02 06:00:00 → ORD 2026-12-02 08:00:00; nonstop; 180 minutes. Local airport times.
  • United Airlines UA1186: ORD 2026-12-08 06:00:00 → BOS 2026-12-08 09:19:00; nonstop; 139 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $300.00

  • Delta Air Lines DL5606: BOS 2026-12-02 20:10:00 → ORD 2026-12-02 22:04:00; nonstop; 174 minutes. Local airport times.
  • Delta Air Lines DL2570: ORD 2026-12-08 10:35:00 → BOS 2026-12-08 13:59:00; nonstop; 144 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $265.00

  • JetBlue Airways B6111: BOS 2026-12-02 09:59:00 → ORD 2026-12-02 12:00:00; nonstop; 181 minutes. Local airport times.
  • JetBlue Airways B6112: ORD 2026-12-08 13:00:00 → BOS 2026-12-08 16:49:00; nonstop; 169 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $290.00

  • American Airlines AA2461: BOS 2026-12-02 17:58:00 → ORD 2026-12-02 20:12:00; nonstop; 194 minutes. Local airport times.
  • American Airlines AA1212: ORD 2026-12-08 19:13:00 → BOS 2026-12-08 22:42:00; nonstop; 149 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $290.00

  • United Airlines UA1414: BOS 2026-12-02 05:45:00 → ORD 2026-12-02 07:51:00; nonstop; 186 minutes. Local airport times.
  • United Airlines UA2213: ORD 2026-12-08 07:00:00 → BOS 2026-12-08 10:19:00; nonstop; 139 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $300.00

  • Delta Air Lines DL2570: BOS 2026-12-02 07:30:00 → ORD 2026-12-02 09:35:00; nonstop; 185 minutes. Local airport times.
  • Delta Air Lines DL2570: ORD 2026-12-08 10:35:00 → BOS 2026-12-08 13:59:00; nonstop; 144 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $300.00

  • American Airlines AA4798 / AA3177: BOS 2026-12-02 15:45:00 → ORD 2026-12-02 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
    • AA4798: BOS 2026-12-02 15:45:00 → PHL 2026-12-02 17:30:00; layover at PHL: 65 minutes.
    • AA3177: PHL 2026-12-02 18:35:00 → ORD 2026-12-02 20:30:00.
  • American Airlines AA1212: ORD 2026-12-08 19:13:00 → BOS 2026-12-08 22:42:00; nonstop; 149 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $300.00

  • American Airlines AA4609 / AA4733: BOS 2026-12-02 10:07:00 → ORD 2026-12-02 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
    • AA4609: BOS 2026-12-02 10:07:00 → CVG 2026-12-02 12:50:00; layover at CVG: 104 minutes.
    • AA4733: CVG 2026-12-02 14:34:00 → ORD 2026-12-02 15:14:00.
  • American Airlines AA1212: ORD 2026-12-08 19:13:00 → BOS 2026-12-08 22:42:00; nonstop; 149 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $300.00

  • American Airlines AA4133 / AA4390: BOS 2026-12-02 10:00:00 → ORD 2026-12-02 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
    • AA4133: BOS 2026-12-02 10:00:00 → SYR 2026-12-02 11:23:00; layover at SYR: 68 minutes.
    • AA4390: SYR 2026-12-02 12:31:00 → ORD 2026-12-02 13:59:00.
  • American Airlines AA1212: ORD 2026-12-08 19:13:00 → BOS 2026-12-08 22:42:00; nonstop; 149 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $302.50

  • United Airlines UA546 / UA703: BOS 2026-12-02 15:42:00 → ORD 2026-12-02 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
    • UA546: BOS 2026-12-02 15:42:00 → EWR 2026-12-02 17:08:00; layover at EWR: 62 minutes.
    • UA703: EWR 2026-12-02 18:10:00 → ORD 2026-12-02 20:06:00.
  • United Airlines UA1186: ORD 2026-12-08 06:00:00 → BOS 2026-12-08 09:19:00; nonstop; 139 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $302.50

  • United Airlines UA721 / UA2497: BOS 2026-12-02 14:40:00 → ORD 2026-12-02 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
    • UA721: BOS 2026-12-02 14:40:00 → IAD 2026-12-02 16:27:00; layover at IAD: 72 minutes.
    • UA2497: IAD 2026-12-02 17:39:00 → ORD 2026-12-02 19:05:00.
  • United Airlines UA1186: ORD 2026-12-08 06:00:00 → BOS 2026-12-08 09:19:00; nonstop; 139 minutes. Local airport times.

2026-12-02 → 2026-12-08 · $312.50

  • Delta Air Lines DL2570: BOS 2026-12-02 07:30:00 → ORD 2026-12-02 09:38:00; nonstop; 188 minutes. Local airport times.
  • Delta Air Lines DL2917 / DL5727: ORD 2026-12-08 10:06:00 → BOS 2026-12-08 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
    • DL2917: ORD 2026-12-08 10:06:00 → LGA 2026-12-08 13:18:00; layover at LGA: 102 minutes.
    • DL5727: LGA 2026-12-08 15:00:00 → BOS 2026-12-08 16:25:00.

More dates for this route