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Route overview: Boston to Chicago (ORD) flight deals

Boston → Chicago

Jun 25, 2027 · return Jun 29, 2027

BOS → ORD1 adulteconomyRound trip

14 flight options · 5 airlines

Nonstop flights

Fri, Jun 25 – Tue, Jun 29

JetBlue Airways
4:45 pmBOS
3h 13m
Nonstop
6:58 pmORD
JetBlue Airways
1:00 pmORD
2h 49m
Nonstop
4:49 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

American Airlines
12:16 pmBOS
3h 12m
Nonstop
2:28 pmORD
American Airlines
10:43 amORD
2h 34m
Nonstop
2:17 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

United Airlines
11:35 amBOS
3h 4m
Nonstop
1:39 pmORD
United Airlines
7:05 amORD
2h 26m
Nonstop
10:31 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

Delta Air Lines
8:59 pmBOS
2h 58m
Nonstop
10:57 pmORD
Delta Air Lines
10:38 amORD
2h 37m
Nonstop
2:15 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

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

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

American Airlines
8:51 amBOS
3h 19m
Nonstop
11:10 amORD
American Airlines
10:43 amORD
2h 34m
Nonstop
2:17 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

United Airlines
2:58 pmBOS
3h 2m
Nonstop
5:00 pmORD
United Airlines
7:05 amORD
2h 26m
Nonstop
10:31 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

Delta Air Lines
4:35 pmBOS
3h 10m
Nonstop
6:45 pmORD
Delta Air Lines
10:38 amORD
2h 37m
Nonstop
2:15 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Fri, Jun 25 – Tue, Jun 29

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

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

American Airlines
10:07 amBOS
6h 7m
CVG · 1h 44m
3:14 pmORD
American Airlines
10:43 amORD
2h 34m
Nonstop
2:17 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

American Airlines
3:45 pmBOS
5h 45m
PHL · 1h 5m
8:30 pmORD
American Airlines
10:43 amORD
2h 34m
Nonstop
2:17 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

United Airlines
2:40 pmBOS
5h 25m
IAD · 1h 12m
7:05 pmORD
United Airlines
7:05 amORD
2h 26m
Nonstop
10:31 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

United Airlines
3:42 pmBOS
5h 24m
EWR · 1h 2m
8:06 pmORD
United Airlines
7:05 amORD
2h 26m
Nonstop
10:31 amBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Jun 25 – Tue, Jun 29

Delta Air Lines
8:40 pmBOS
2h 56m
Nonstop
10:36 pmORD
Delta Air Lines
10:06 amORD
5h 19m
LGA · 1h 42m
4:25 pmBOS

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

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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Explore this route

All dates for this routeJun 24, 2027 · Return optionsJun 26, 2027 · Return optionsHotels in Chicago with Axel
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.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-06-25 → 2027-06-29JetBlue AirwaysB6811 / B6112Axel-exclusive $310.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29American AirlinesAA581 / AA2779Axel-exclusive $335.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29United AirlinesUA2342 / UA2402Axel-exclusive $335.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29Delta Air LinesDL2804 / DL2570Axel-exclusive $345.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29Air CanadaAC8695 + AC511 / AC508 + AC772Axel-exclusive $495.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29JetBlue AirwaysB6111 / B6112Axel-exclusive $310.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29American AirlinesAA4579 / AA2779Axel-exclusive $335.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29United AirlinesUA2496 / UA2402Axel-exclusive $335.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29Delta Air LinesDL2646 / DL2570Axel-exclusive $345.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29American AirlinesAA4609 + AA4733 / AA2779Axel-exclusive $345.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29American AirlinesAA4798 + AA3177 / AA2779Axel-exclusive $345.002026-10-29T00:52:35Z
2027-06-25 → 2027-06-29United AirlinesUA721 + UA2497 / UA2402Axel-exclusive $347.502026-10-29T00:52:35Z
2027-06-25 → 2027-06-29United AirlinesUA546 + UA703 / UA2402Axel-exclusive $347.502026-10-29T00:52:35Z
2027-06-25 → 2027-06-29Delta Air LinesDL2804 / DL2917 + DL5727Axel-exclusive $355.002026-10-29T00:52:35Z

Route overview: Boston to Chicago (ORD) flight deals

2027-06-25 → 2027-06-29 · Axel-exclusive $310.00

  • JetBlue Airways B6811: BOS 2027-06-25 16:45:00 → ORD 2027-06-25 18:58:00; nonstop; 193 minutes. Local airport times.
  • JetBlue Airways B6112: ORD 2027-06-29 13:00:00 → BOS 2027-06-29 16:49:00; nonstop; 169 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $335.00

  • American Airlines AA581: BOS 2027-06-25 12:16:00 → ORD 2027-06-25 14:28:00; nonstop; 192 minutes. Local airport times.
  • American Airlines AA2779: ORD 2027-06-29 10:43:00 → BOS 2027-06-29 14:17:00; nonstop; 154 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $335.00

  • United Airlines UA2342: BOS 2027-06-25 11:35:00 → ORD 2027-06-25 13:39:00; nonstop; 184 minutes. Local airport times.
  • United Airlines UA2402: ORD 2027-06-29 07:05:00 → BOS 2027-06-29 10:31:00; nonstop; 146 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $345.00

  • Delta Air Lines DL2804: BOS 2027-06-25 20:59:00 → ORD 2027-06-25 22:57:00; nonstop; 178 minutes. Local airport times.
  • Delta Air Lines DL2570: ORD 2027-06-29 10:38:00 → BOS 2027-06-29 14:15:00; nonstop; 157 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $495.00

  • Air Canada AC8695 / AC511: BOS 2027-06-25 15:10:00 → ORD 2027-06-25 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
    • AC8695: BOS 2027-06-25 15:10:00 → YYZ 2027-06-25 17:11:00; layover at YYZ: 104 minutes.
    • AC511: YYZ 2027-06-25 18:55:00 → ORD 2027-06-25 19:58:00.
  • Air Canada AC508 / AC772: ORD 2027-06-29 16:30:00 → BOS 2027-06-29 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
    • AC508: ORD 2027-06-29 16:30:00 → YYZ 2027-06-29 19:10:00; layover at YYZ: 105 minutes.
    • AC772: YYZ 2027-06-29 20:55:00 → BOS 2027-06-29 22:37:00.

2027-06-25 → 2027-06-29 · Axel-exclusive $310.00

  • JetBlue Airways B6111: BOS 2027-06-25 09:59:00 → ORD 2027-06-25 12:00:00; nonstop; 181 minutes. Local airport times.
  • JetBlue Airways B6112: ORD 2027-06-29 13:00:00 → BOS 2027-06-29 16:49:00; nonstop; 169 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $335.00

  • American Airlines AA4579: BOS 2027-06-25 08:51:00 → ORD 2027-06-25 11:10:00; nonstop; 199 minutes. Local airport times.
  • American Airlines AA2779: ORD 2027-06-29 10:43:00 → BOS 2027-06-29 14:17:00; nonstop; 154 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $335.00

  • United Airlines UA2496: BOS 2027-06-25 14:58:00 → ORD 2027-06-25 17:00:00; nonstop; 182 minutes. Local airport times.
  • United Airlines UA2402: ORD 2027-06-29 07:05:00 → BOS 2027-06-29 10:31:00; nonstop; 146 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $345.00

  • Delta Air Lines DL2646: BOS 2027-06-25 16:35:00 → ORD 2027-06-25 18:45:00; nonstop; 190 minutes. Local airport times.
  • Delta Air Lines DL2570: ORD 2027-06-29 10:38:00 → BOS 2027-06-29 14:15:00; nonstop; 157 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $345.00

  • American Airlines AA4609 / AA4733: BOS 2027-06-25 10:07:00 → ORD 2027-06-25 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
    • AA4609: BOS 2027-06-25 10:07:00 → CVG 2027-06-25 12:50:00; layover at CVG: 104 minutes.
    • AA4733: CVG 2027-06-25 14:34:00 → ORD 2027-06-25 15:14:00.
  • American Airlines AA2779: ORD 2027-06-29 10:43:00 → BOS 2027-06-29 14:17:00; nonstop; 154 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $345.00

  • American Airlines AA4798 / AA3177: BOS 2027-06-25 15:45:00 → ORD 2027-06-25 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
    • AA4798: BOS 2027-06-25 15:45:00 → PHL 2027-06-25 17:30:00; layover at PHL: 65 minutes.
    • AA3177: PHL 2027-06-25 18:35:00 → ORD 2027-06-25 20:30:00.
  • American Airlines AA2779: ORD 2027-06-29 10:43:00 → BOS 2027-06-29 14:17:00; nonstop; 154 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $347.50

  • United Airlines UA721 / UA2497: BOS 2027-06-25 14:40:00 → ORD 2027-06-25 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
    • UA721: BOS 2027-06-25 14:40:00 → IAD 2027-06-25 16:27:00; layover at IAD: 72 minutes.
    • UA2497: IAD 2027-06-25 17:39:00 → ORD 2027-06-25 19:05:00.
  • United Airlines UA2402: ORD 2027-06-29 07:05:00 → BOS 2027-06-29 10:31:00; nonstop; 146 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $347.50

  • United Airlines UA546 / UA703: BOS 2027-06-25 15:42:00 → ORD 2027-06-25 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
    • UA546: BOS 2027-06-25 15:42:00 → EWR 2027-06-25 17:08:00; layover at EWR: 62 minutes.
    • UA703: EWR 2027-06-25 18:10:00 → ORD 2027-06-25 20:06:00.
  • United Airlines UA2402: ORD 2027-06-29 07:05:00 → BOS 2027-06-29 10:31:00; nonstop; 146 minutes. Local airport times.

2027-06-25 → 2027-06-29 · Axel-exclusive $355.00

  • Delta Air Lines DL2804: BOS 2027-06-25 20:40:00 → ORD 2027-06-25 22:36:00; nonstop; 176 minutes. Local airport times.
  • Delta Air Lines DL2917 / DL5727: ORD 2027-06-29 10:06:00 → BOS 2027-06-29 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
    • DL2917: ORD 2027-06-29 10:06:00 → LGA 2027-06-29 13:18:00; layover at LGA: 102 minutes.
    • DL5727: LGA 2027-06-29 15:00:00 → BOS 2027-06-29 16:25:00.

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For AI assistants

  • This page: Boston (BOS) to Chicago (ORD) · Jun 25, 2027 · return Jun 29, 2027: 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. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. 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.