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Route overview: Chicago to Boston (BOS) flight deals

Chicago → Boston

Nov 21, 2026 · return Dec 1, 2026

ORD → BOS1 adulteconomyRound trip

13 flight options · 5 airlines

Nonstop flights

Sat, Nov 21 – Tue, Dec 1

JetBlue Airways
1:00 pmORD
2h 49m
Nonstop
4:49 pmBOS
JetBlue Airways
2:40 pmBOS
3h 2m
Nonstop
4:42 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

American Airlines
5:52 pmORD
2h 24m
Nonstop
9:16 pmBOS
American Airlines
12:33 pmBOS
3h 7m
Nonstop
2:40 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

United Airlines
7:00 amORD
2h 19m
Nonstop
10:19 amBOS
United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

Delta Air Lines
12:35 pmORD
2h 30m
Nonstop
4:05 pmBOS
Delta Air Lines
7:30 amBOS
3h 8m
Nonstop
9:38 amORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

American Airlines
6:00 amORD
2h 24m
Nonstop
9:24 amBOS
American Airlines
12:33 pmBOS
3h 7m
Nonstop
2:40 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

United Airlines
9:20 pmORD
2h 26m
Nonstop
12:46 am+1BOS
United Airlines
6:00 amBOS
3h
Nonstop
8:00 amORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

Delta Air Lines
7:05 amORD
2h 28m
Nonstop
10:33 amBOS
Delta Air Lines
7:30 amBOS
3h 8m
Nonstop
9:38 amORD

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, Nov 21 – Tue, Dec 1

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

Sat, Nov 21 – Tue, Dec 1

American Airlines
8:00 amORD
5h 17m
ROC · 1h 54m
2:17 pmBOS
American Airlines
12:33 pmBOS
3h 7m
Nonstop
2:40 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

American Airlines
3:19 pmORD
5h
PHL · 1h 25m
9:19 pmBOS
American Airlines
12:33 pmBOS
3h 7m
Nonstop
2:40 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

American Airlines
8:00 amORD
5h 9m
BUF · 1h 45m
2:09 pmBOS
American Airlines
12:33 pmBOS
3h 7m
Nonstop
2:40 pmORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

Delta Air Lines
10:06 amORD
5h 19m
LGA · 1h 42m
4:25 pmBOS
Delta Air Lines
7:30 amBOS
3h 8m
Nonstop
9:38 amORD

Round-trip total · 1 adult · Taxes included

Sat, Nov 21 – Tue, Dec 1

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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Explore this route

All dates for this routeNov 20, 2026 → Nov 30, 2026Nov 22, 2026 → Dec 2, 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: Chicago to Boston (BOS) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-11-21 → 2026-12-01JetBlue AirwaysB6112 / B6811$265.002026-10-29T01:52:47Z
2026-11-21 → 2026-12-01American AirlinesAA469 / AA894$290.002026-10-29T01:52:47Z
2026-11-21 → 2026-12-01United AirlinesUA2213 / UA1414$300.002026-10-29T01:52:47Z
2026-11-21 → 2026-12-01Delta Air LinesDL5855 / DL2570$300.002026-10-29T01:52:47Z
2026-11-21 → 2026-12-01Air CanadaAC508 + AC772 / AC8695 + AC511$420.002026-10-29T01:52:47Z
2026-11-21 → 2026-12-01American AirlinesAA1515 / AA894$290.002026-10-29T01:52:47Z
2026-11-21 → 2026-12-01United AirlinesUA2296 / UA1414$300.002026-10-29T01:52:47Z
2026-11-21 → 2026-12-01Delta Air LinesDL5688 / DL2570$300.002026-10-29T01:52:47Z
2026-11-21 → 2026-12-01American AirlinesAA3437 + AA4533 / AA894$282.502026-10-29T01:52:47Z
2026-11-21 → 2026-12-01American AirlinesAA2840 + AA1776 / AA894$282.502026-10-29T01:52:47Z
2026-11-21 → 2026-12-01American AirlinesAA4780 + AA4026 / AA894$282.502026-10-29T01:52:47Z
2026-11-21 → 2026-12-01Delta Air LinesDL2917 + DL5727 / DL2570$292.502026-10-29T01:52:47Z
2026-11-21 → 2026-12-01United AirlinesUA1128 + UA688 / UA1414$292.502026-10-29T01:52:47Z

2026-11-21 → 2026-12-01 · $265.00

  • JetBlue Airways B6112: ORD 2026-11-21 13:00:00 → BOS 2026-11-21 16:49:00; nonstop; 169 minutes. Local airport times.
  • JetBlue Airways B6811: BOS 2026-12-01 14:40:00 → ORD 2026-12-01 16:42:00; nonstop; 182 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $290.00

  • American Airlines AA469: ORD 2026-11-21 17:52:00 → BOS 2026-11-21 21:16:00; nonstop; 144 minutes. Local airport times.
  • American Airlines AA894: BOS 2026-12-01 12:33:00 → ORD 2026-12-01 14:40:00; nonstop; 187 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $300.00

  • United Airlines UA2213: ORD 2026-11-21 07:00:00 → BOS 2026-11-21 10:19:00; nonstop; 139 minutes. Local airport times.
  • United Airlines UA1414: BOS 2026-12-01 06:00:00 → ORD 2026-12-01 08:00:00; nonstop; 180 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $300.00

  • Delta Air Lines DL5855: ORD 2026-11-21 12:35:00 → BOS 2026-11-21 16:05:00; nonstop; 150 minutes. Local airport times.
  • Delta Air Lines DL2570: BOS 2026-12-01 07:30:00 → ORD 2026-12-01 09:38:00; nonstop; 188 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $420.00

  • Air Canada AC508 / AC772: ORD 2026-11-21 16:30:00 → BOS 2026-11-21 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
    • AC508: ORD 2026-11-21 16:30:00 → YYZ 2026-11-21 19:10:00; layover at YYZ: 105 minutes.
    • AC772: YYZ 2026-11-21 20:55:00 → BOS 2026-11-21 22:37:00.
  • Air Canada AC8695 / AC511: BOS 2026-12-01 15:10:00 → ORD 2026-12-01 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
    • AC8695: BOS 2026-12-01 15:10:00 → YYZ 2026-12-01 17:11:00; layover at YYZ: 104 minutes.
    • AC511: YYZ 2026-12-01 18:55:00 → ORD 2026-12-01 19:58:00.

2026-11-21 → 2026-12-01 · $290.00

  • American Airlines AA1515: ORD 2026-11-21 06:00:00 → BOS 2026-11-21 09:24:00; nonstop; 144 minutes. Local airport times.
  • American Airlines AA894: BOS 2026-12-01 12:33:00 → ORD 2026-12-01 14:40:00; nonstop; 187 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $300.00

  • United Airlines UA2296: ORD 2026-11-21 21:20:00 → BOS 2026-11-22 00:46:00; nonstop; 146 minutes. Local airport times.
  • United Airlines UA1414: BOS 2026-12-01 06:00:00 → ORD 2026-12-01 08:00:00; nonstop; 180 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $300.00

  • Delta Air Lines DL5688: ORD 2026-11-21 07:05:00 → BOS 2026-11-21 10:33:00; nonstop; 148 minutes. Local airport times.
  • Delta Air Lines DL2570: BOS 2026-12-01 07:30:00 → ORD 2026-12-01 09:38:00; nonstop; 188 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $282.50

  • American Airlines AA3437 / AA4533: ORD 2026-11-21 08:00:00 → BOS 2026-11-21 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
    • AA3437: ORD 2026-11-21 08:00:00 → ROC 2026-11-21 10:56:00; layover at ROC: 114 minutes.
    • AA4533: ROC 2026-11-21 12:50:00 → BOS 2026-11-21 14:17:00.
  • American Airlines AA894: BOS 2026-12-01 12:33:00 → ORD 2026-12-01 14:40:00; nonstop; 187 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $282.50

  • American Airlines AA2840 / AA1776: ORD 2026-11-21 15:19:00 → BOS 2026-11-21 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
    • AA2840: ORD 2026-11-21 15:19:00 → PHL 2026-11-21 18:30:00; layover at PHL: 85 minutes.
    • AA1776: PHL 2026-11-21 19:55:00 → BOS 2026-11-21 21:19:00.
  • American Airlines AA894: BOS 2026-12-01 12:33:00 → ORD 2026-12-01 14:40:00; nonstop; 187 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $282.50

  • American Airlines AA4780 / AA4026: ORD 2026-11-21 08:00:00 → BOS 2026-11-21 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
    • AA4780: ORD 2026-11-21 08:00:00 → BUF 2026-11-21 10:45:00; layover at BUF: 105 minutes.
    • AA4026: BUF 2026-11-21 12:30:00 → BOS 2026-11-21 14:09:00.
  • American Airlines AA894: BOS 2026-12-01 12:33:00 → ORD 2026-12-01 14:40:00; nonstop; 187 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $292.50

  • Delta Air Lines DL2917 / DL5727: ORD 2026-11-21 10:06:00 → BOS 2026-11-21 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
    • DL2917: ORD 2026-11-21 10:06:00 → LGA 2026-11-21 13:18:00; layover at LGA: 102 minutes.
    • DL5727: LGA 2026-11-21 15:00:00 → BOS 2026-11-21 16:25:00.
  • Delta Air Lines DL2570: BOS 2026-12-01 07:30:00 → ORD 2026-12-01 09:38:00; nonstop; 188 minutes. Local airport times.

2026-11-21 → 2026-12-01 · $292.50

  • United Airlines UA1128 / UA688: ORD 2026-11-21 13:00:00 → BOS 2026-11-21 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
    • UA1128: ORD 2026-11-21 13:00:00 → IAD 2026-11-21 16:03:00; layover at IAD: 72 minutes.
    • UA688: IAD 2026-11-21 17:15:00 → BOS 2026-11-21 18:57:00.
  • United Airlines UA1414: BOS 2026-12-01 06:00:00 → ORD 2026-12-01 08:00:00; nonstop; 180 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Chicago (ORD) to Boston (BOS) · Nov 21, 2026 · return Dec 1, 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 Chicago to Boston (BOS) 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.