ORD → BOS

Find and Compare the Cheapest Ways to Fly from Chicago to Boston

Compare one-way, round-trip and flight + hotel packages from Chicago to Boston, a nonstop flight of about 2h 15m, with fares from around 160. Nonstop fares seen from JetBlue, American and United.

Chicago to Boston flight facts

Chicago to Boston is a domestic route covering about 863 miles, arriving at Boston Logan International Airport (BOS) in United States. Peak travel season in Boston runs June–October (warm summers, fall foliage), while December–March is usually the quietest and best-value time to visit. Nonstop fares we've tracked on this route come from JetBlue, American and United.

Key facts for flights from Chicago to Boston
Departing fromO'Hare International Airport (ORD)
Arriving atBoston Logan International Airport (BOS)
Distance863 miles (1,390 km)
Nonstop flight timeAbout 2h 15m
Nonstop airlines seenJetBlue, American and United
Round-trip fares from$160 (estimate)
Cheapest monthsSeptember, May, October
Peak season in BostonJune–October
Cheapest hotel months in BostonDecember–March
Best time to book1 to 3 months ahead
Route info updatedOctober 16, 2026

When to visit Boston

  • Peak season

    June–October

    Warm summers, fall foliage

  • Shoulder season

    April–May & November

    Cool and changeable

  • Off-peak season

    December–March

    Cold with frequent snow

Estimated round-trip fares by month, Chicago to Boston

Estimated lowest round-trip fare per month
MonthFares from
January$185
February$175
March$190
April$180
May$165
June$235
July$225
August$225
September$160
October$165
November$210
December$220

Flying from Chicago to Boston

Airlines Flying this Route

Nonstop fares we've tracked on this route come from JetBlue, American and United. Ducoffs.com compares full-service and low-cost airlines flying between Chicago and Boston in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.

Best Time to Book Flights from Chicago to Boston

Fares on this route tend to be lowest in September, May, and October. For the best selection, book about 1 to 3 months before departure and stay flexible by a day or two.

Average Travel Duration

Chicago and Boston are about 863 miles apart. A nonstop flight takes roughly 2h 15m; connecting itineraries usually add 2 to 5 hours.

Chicago to Boston flight questions

How can I find the absolute cheapest flight from Chicago to Boston?

The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.

What is the cheapest month to fly from Chicago to Boston?

Based on typical seasonal demand, September, May, and October tend to offer the lowest fares on this route, with estimated round-trip prices starting around $160. Live prices change daily, so run a search for your exact dates.

How long is the flight from Chicago to Boston?

Chicago and Boston are about 863 miles apart. A nonstop flight takes roughly 2h 15m, while connecting itineraries usually add 2 to 5 hours depending on the layover.

Which airlines fly nonstop from Chicago to Boston?

Recent nonstop fares we've tracked on this route come from JetBlue, American and United. Schedules change by season, so your live search shows every airline flying your dates.

When are hotels cheapest in Boston?

Hotel rates in Boston are usually lowest in December–March, when demand is quieter, and highest during peak season (June–October). Booking your flight and hotel together can save up to 30%.

Which airport do I fly into for Boston?

This route arrives at Boston Logan International Airport (BOS). Your search results also show nearby airports when they offer a cheaper or faster option.

How far in advance should I book a flight to Boston?

For this route, booking about 1 to 3 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.

Is it cheaper to bundle flights and hotels together?

Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.