Travel with Axel,
get the best price.

Route overview: Boston to Chicago (ORD) flight deals

Boston → Chicago

Dec 5, 2026 · return Dec 9, 2026

BOS → ORD1 adulteconomyRound trip

14 flight options · 5 airlines

Nonstop flights

Sat, Dec 5 – Wed, Dec 9

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

Sat, Dec 5 – Wed, Dec 9

American Airlines
7:37 amBOS
3h 22m
Nonstop
9:59 amORD
American Airlines
6:00 amORD
2h 24m
Nonstop
9:24 amBOS

Round-trip total · 1 adult · Taxes included

Sat, Dec 5 – Wed, Dec 9

United Airlines
7:31 amBOS
3h
Nonstop
9:31 amORD
United Airlines
7:00 amORD
2h 19m
Nonstop
10:19 amBOS

Round-trip total · 1 adult · Taxes included

Sat, Dec 5 – Wed, Dec 9

Delta Air Lines
2:55 pmBOS
3h 6m
Nonstop
5:01 pmORD
Delta Air Lines
10:35 amORD
2h 24m
Nonstop
1:59 pmBOS

Round-trip total · 1 adult · Taxes included

Sat, Dec 5 – Wed, Dec 9

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

Sat, Dec 5 – Wed, Dec 9

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

Round-trip total · 1 adult · Taxes included

Sat, Dec 5 – Wed, Dec 9

United Airlines
6:38 pmBOS
3h 2m
Nonstop
8:40 pmORD
United Airlines
7:00 amORD
2h 19m
Nonstop
10:19 amBOS

Round-trip total · 1 adult · Taxes included

Sat, Dec 5 – Wed, Dec 9

Delta Air Lines
6:15 pmBOS
3h 11m
Nonstop
8:26 pmORD
Delta Air Lines
10:35 amORD
2h 24m
Nonstop
1:59 pmBOS

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, Dec 5 – Wed, Dec 9

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

Sat, Dec 5 – Wed, Dec 9

American Airlines
10:00 amBOS
4h 59m
SYR · 1h 8m
1:59 pmORD
American Airlines
6:00 amORD
2h 24m
Nonstop
9:24 amBOS

Round-trip total · 1 adult · Taxes included

Sat, Dec 5 – Wed, Dec 9

American Airlines
3:45 pmBOS
5h 45m
PHL · 1h 5m
8:30 pmORD
American Airlines
6:00 amORD
2h 24m
Nonstop
9:24 amBOS

Round-trip total · 1 adult · Taxes included

Sat, Dec 5 – Wed, Dec 9

American Airlines
10:07 amBOS
6h 7m
CVG · 1h 44m
3:14 pmORD
American Airlines
6:00 amORD
2h 24m
Nonstop
9:24 amBOS

Round-trip total · 1 adult · Taxes included

Sat, Dec 5 – Wed, Dec 9

United Airlines
3:42 pmBOS
5h 24m
EWR · 1h 2m
8:06 pmORD
United Airlines
7:00 amORD
2h 19m
Nonstop
10:19 amBOS

Round-trip total · 1 adult · Taxes included

Sat, Dec 5 – Wed, Dec 9

United Airlines
2:40 pmBOS
5h 25m
IAD · 1h 12m
7:05 pmORD
United Airlines
7:00 amORD
2h 19m
Nonstop
10:19 amBOS

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.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, JetBlue Airways emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

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

Explore this route

All dates for this routeDec 4, 2026 → Dec 8, 2026Dec 6, 2026 → Dec 10, 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: Boston to Chicago (ORD) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-05 → 2026-12-09JetBlue AirwaysB6611 / B61012$265.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09American AirlinesAA947 / AA1515$290.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09United AirlinesUA1834 / UA2213$290.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09Delta Air LinesDL5611 / DL2570$300.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09Air CanadaAC8695 + AC511 / AC508 + AC772$440.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09JetBlue AirwaysB6111 / B61012$265.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09American AirlinesAA894 / AA1515$290.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09United AirlinesUA1015 / UA2213$290.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09Delta Air LinesDL5617 / DL2570$300.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09American AirlinesAA4133 + AA4390 / AA1515$300.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09American AirlinesAA4798 + AA3177 / AA1515$300.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09American AirlinesAA4609 + AA4733 / AA1515$300.002026-10-29T00:52:35Z
2026-12-05 → 2026-12-09United AirlinesUA546 + UA703 / UA2213$302.502026-10-29T00:52:35Z
2026-12-05 → 2026-12-09United AirlinesUA721 + UA2497 / UA2213$302.502026-10-29T00:52:35Z

2026-12-05 → 2026-12-09 · $265.00

  • JetBlue Airways B6611: BOS 2026-12-05 14:40:00 → ORD 2026-12-05 16:40:00; nonstop; 180 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2026-12-09 17:46:00 → BOS 2026-12-09 21:14:00; nonstop; 148 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $290.00

  • American Airlines AA947: BOS 2026-12-05 07:37:00 → ORD 2026-12-05 09:59:00; nonstop; 202 minutes. Local airport times.
  • American Airlines AA1515: ORD 2026-12-09 06:00:00 → BOS 2026-12-09 09:24:00; nonstop; 144 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $290.00

  • United Airlines UA1834: BOS 2026-12-05 07:31:00 → ORD 2026-12-05 09:31:00; nonstop; 180 minutes. Local airport times.
  • United Airlines UA2213: ORD 2026-12-09 07:00:00 → BOS 2026-12-09 10:19:00; nonstop; 139 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $300.00

  • Delta Air Lines DL5611: BOS 2026-12-05 14:55:00 → ORD 2026-12-05 17:01:00; nonstop; 186 minutes. Local airport times.
  • Delta Air Lines DL2570: ORD 2026-12-09 10:35:00 → BOS 2026-12-09 13:59:00; nonstop; 144 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $440.00

  • Air Canada AC8695 / AC511: BOS 2026-12-05 15:10:00 → ORD 2026-12-05 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
    • AC8695: BOS 2026-12-05 15:10:00 → YYZ 2026-12-05 17:11:00; layover at YYZ: 104 minutes.
    • AC511: YYZ 2026-12-05 18:55:00 → ORD 2026-12-05 19:58:00.
  • Air Canada AC508 / AC772: ORD 2026-12-09 16:30:00 → BOS 2026-12-09 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
    • AC508: ORD 2026-12-09 16:30:00 → YYZ 2026-12-09 19:10:00; layover at YYZ: 105 minutes.
    • AC772: YYZ 2026-12-09 20:55:00 → BOS 2026-12-09 22:37:00.

2026-12-05 → 2026-12-09 · $265.00

  • JetBlue Airways B6111: BOS 2026-12-05 09:59:00 → ORD 2026-12-05 12:00:00; nonstop; 181 minutes. Local airport times.
  • JetBlue Airways B61012: ORD 2026-12-09 17:46:00 → BOS 2026-12-09 21:14:00; nonstop; 148 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $290.00

  • American Airlines AA894: BOS 2026-12-05 12:33:00 → ORD 2026-12-05 14:40:00; nonstop; 187 minutes. Local airport times.
  • American Airlines AA1515: ORD 2026-12-09 06:00:00 → BOS 2026-12-09 09:24:00; nonstop; 144 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $290.00

  • United Airlines UA1015: BOS 2026-12-05 18:38:00 → ORD 2026-12-05 20:40:00; nonstop; 182 minutes. Local airport times.
  • United Airlines UA2213: ORD 2026-12-09 07:00:00 → BOS 2026-12-09 10:19:00; nonstop; 139 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $300.00

  • Delta Air Lines DL5617: BOS 2026-12-05 18:15:00 → ORD 2026-12-05 20:26:00; nonstop; 191 minutes. Local airport times.
  • Delta Air Lines DL2570: ORD 2026-12-09 10:35:00 → BOS 2026-12-09 13:59:00; nonstop; 144 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $300.00

  • American Airlines AA4133 / AA4390: BOS 2026-12-05 10:00:00 → ORD 2026-12-05 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
    • AA4133: BOS 2026-12-05 10:00:00 → SYR 2026-12-05 11:23:00; layover at SYR: 68 minutes.
    • AA4390: SYR 2026-12-05 12:31:00 → ORD 2026-12-05 13:59:00.
  • American Airlines AA1515: ORD 2026-12-09 06:00:00 → BOS 2026-12-09 09:24:00; nonstop; 144 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $300.00

  • American Airlines AA4798 / AA3177: BOS 2026-12-05 15:45:00 → ORD 2026-12-05 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
    • AA4798: BOS 2026-12-05 15:45:00 → PHL 2026-12-05 17:30:00; layover at PHL: 65 minutes.
    • AA3177: PHL 2026-12-05 18:35:00 → ORD 2026-12-05 20:30:00.
  • American Airlines AA1515: ORD 2026-12-09 06:00:00 → BOS 2026-12-09 09:24:00; nonstop; 144 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $300.00

  • American Airlines AA4609 / AA4733: BOS 2026-12-05 10:07:00 → ORD 2026-12-05 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
    • AA4609: BOS 2026-12-05 10:07:00 → CVG 2026-12-05 12:50:00; layover at CVG: 104 minutes.
    • AA4733: CVG 2026-12-05 14:34:00 → ORD 2026-12-05 15:14:00.
  • American Airlines AA1515: ORD 2026-12-09 06:00:00 → BOS 2026-12-09 09:24:00; nonstop; 144 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $302.50

  • United Airlines UA546 / UA703: BOS 2026-12-05 15:42:00 → ORD 2026-12-05 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
    • UA546: BOS 2026-12-05 15:42:00 → EWR 2026-12-05 17:08:00; layover at EWR: 62 minutes.
    • UA703: EWR 2026-12-05 18:10:00 → ORD 2026-12-05 20:06:00.
  • United Airlines UA2213: ORD 2026-12-09 07:00:00 → BOS 2026-12-09 10:19:00; nonstop; 139 minutes. Local airport times.

2026-12-05 → 2026-12-09 · $302.50

  • United Airlines UA721 / UA2497: BOS 2026-12-05 14:40:00 → ORD 2026-12-05 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
    • UA721: BOS 2026-12-05 14:40:00 → IAD 2026-12-05 16:27:00; layover at IAD: 72 minutes.
    • UA2497: IAD 2026-12-05 17:39:00 → ORD 2026-12-05 19:05:00.
  • United Airlines UA2213: ORD 2026-12-09 07:00:00 → BOS 2026-12-09 10:19:00; nonstop; 139 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Boston (BOS) to Chicago (ORD) · Dec 5, 2026 · return Dec 9, 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 Boston to Chicago (ORD) 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.