Chicago (ORD) to Boston (BOS) · Aug 24, 2027 · choose your return date

Chicago (ORD) to Boston (BOS): round-trip and one-way prices for 1 departure dates, Aug 24, 2027–Aug 24, 2027. One adult, economy. Open a departure for return options; use the chooser below for other travelers and cabins.

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

August 2027: Aug 24 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 August 2027: price by departure date

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

Tue, Aug 24, 2027 | return Aug 25, Aug 29–30, Sep 3, Sep 8–10, Sep 12–15, Sep 17–19, Sep 21, Sep 23, Sep 25, Sep 27–28, Oct 1–4, Oct 6, Oct 8 · United $335 | return Aug 26–28, Aug 31–Sep 2, Sep 4–7, Sep 11, Sep 16, Sep 20, Sep 22, Sep 24, Sep 26, Sep 29–30, Oct 5, Oct 7 · American $335 | one-way · American $167 | Aug 25 · Aug 26 · Aug 27 · Aug 28 · Aug 29 · Aug 30 · Aug 31 · Sep 1 · Sep 2 · Sep 3 · Sep 4 · Sep 5 · Sep 6 · Sep 7 · Sep 8 · Sep 9 · Sep 10 · Sep 11 · Sep 12 · Sep 13 · Sep 14 · Sep 15 · Sep 16 · Sep 17 · Sep 18 · Sep 19 · Sep 20 · Sep 21 · Sep 22 · 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 Aug 24, 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) · Aug 24, 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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