Chicago (ORD) to Boston (BOS) · Apr 21, 2027 · choose your return date

Chicago (ORD) to Boston (BOS): round-trip and one-way prices for 1 departure dates, Apr 21, 2027–Apr 21, 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 27m outbound; 2h 47m–3h 5m 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

April 2027: Apr 21 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 April 2027: price by departure date

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

Wed, Apr 21, 2027 | return Apr 22, Apr 27, Apr 30–May 2, May 4, May 6–7, May 9–10, May 13–14, May 18, May 20–25, May 27–28, May 30–Jun 1, Jun 6, Jun 8–9, Jun 11, Jun 14, Jun 16, Jun 20, Jun 22, Jun 24, Jun 28–Jul 1, Jul 4, Jul 7–9, Jul 15–16, Jul 18–19 · American $335 | return Apr 23, Apr 26 · American $407 | return Apr 24–25 · United $407 | return Apr 28–29, May 3, May 5, May 8, May 11–12, May 15–17, May 19, May 26, May 29, Jun 2–5, Jun 7, Jun 10, Jun 12–13, Jun 15, Jun 17–19, Jun 21, Jun 23, Jun 25–27, Jul 2–3, Jul 5–6, Jul 10–14, Jul 17, Jul 20 · United $335 | one-way · American $167 | Apr 22 · Apr 23 · Apr 24 · Apr 25 · Apr 26 · Apr 27 · Apr 28 · Apr 29 · Apr 30 · May 1 · May 2 · May 3 · May 4 · May 5 · May 6 · May 7 · May 8 · May 9 · May 10 · May 11 · May 12 · May 13 · May 14 · May 15 · May 16 · May 17 · May 18 · May 19 · May 20 · May 21 · May 22 · May 23 · May 24 · May 25 · May 26 · May 27 · May 28 · May 29 · May 30 · May 31 · Jun 1 · Jun 2 · Jun 3 · Jun 4 · Jun 5 · Jun 6 · Jun 7 · Jun 8 · Jun 9 · Jun 10 · Jun 11 · Jun 12 · Jun 13 · Jun 14 · Jun 15 · Jun 16 · Jun 17 · Jun 18 · Jun 19 · Jun 20 · Jun 21 · Jun 22 · Jun 23 · Jun 24 · Jun 25 · Jun 26 · Jun 27 · Jun 28 · Jun 29 · Jun 30 · Jul 1 · Jul 2 · Jul 3 · Jul 4 · Jul 5 · Jul 6 · Jul 7 · Jul 8 · Jul 9 · Jul 10 · Jul 11 · Jul 12 · Jul 13 · Jul 14 · Jul 15 · Jul 16 · Jul 17 · Jul 18 · Jul 19 · Jul 20
Hotels in Boston from Apr 21, 2027 (per night, 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $200 a night · 4★ The Colonnade Hotel Back Bay, $306 a night · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $507 a night

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Apr 21, 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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