Chicago (ORD) to Boston (BOS) · Sep 22, 2027 · choose your return date

Chicago (ORD) to Boston (BOS): round-trip and one-way prices for 1 departure dates, Sep 22, 2027–Sep 22, 2027. One adult, economy. Open a departure for return options; use the chooser below for other travelers and cabins.

American, nonstop, from $335 round trip · United, nonstop, from $335 round trip

Ticketing airlines with departures in this calendar: American Airlines, JetBlue Airways, United Airlines.

Saved nonstop flight times: 2h 23m–2h 29m outbound; 2h 47m–3h 1m returning.

How to read the calendar: published Axel-exclusive USD totals for one adult, including required taxes; basic economy may apply. Each return range includes its own prices. Only the listed dates and options are priced. Date links open published details; live search checks availability and lets you select flights.

To open an exact round trip, append /mon-d for the return to the departure URL (for example /dec-13), or /one-way for a one-way trip.

Hotels: under a departure date, hotels in Boston link to each hotel's page for that arrival date, where every stay length is priced for 2 adults in 1 room. When a price is shown, it is the nightly rate over the first 3 nights, from the lowest saved total among the shortlisted hotels in that star tier.

Chicago to Boston flight prices by month

September 2027: Sep 22 from $335.

Month summaries show the lowest displayed round-trip total for each departure. Match your return date to the calendar below.

Chicago to Boston flights in September 2027: price by departure date

ORD → BOS · USD · 1 adult · economy · published Nov 12, 2026

Wed, Sep 22, 2027 | return Sep 23–24, Sep 26, Sep 30–Oct 2, Oct 4, Oct 6 · United $335 | return Sep 25, Sep 27–29, Oct 3, Oct 5, Oct 7–8 · American $335 | one-way · United $167 | Sep 23 · Sep 24 · Sep 25 · Sep 26 · Sep 27 · Sep 28 · Sep 29 · Sep 30 · Oct 1 · Oct 2 · Oct 3 · Oct 4 · Oct 5 · Oct 6 · Oct 7 · Oct 8
Hotels in Boston from Sep 22, 2027 (per night, 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Dagny Boston · 5★ Boston Harbor Hotel

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Sep 22, 2027 · choose your return date: 1 adult in economy, no fare priced at the moment. Under a trip, hotels in Boston for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: no fare is priced here right now. Choose travelers and dates and enter the traveler's own trip there for live prices.
• 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. 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.

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