Route guide · 858 miles
Cheap Flights from Chicago to Boston
MDW → BOS · Nonstop 2h 15m · Live round-trip fares
If Boston is next on your list, here's the honest picture on fares from Chicago. The trip covers about 858 miles and takes roughly 2h 15m in the air. Prices on this route reward planners: booking 3–6 weeks ahead is the sweet spot, and the lowest fares tend to sell out fast.
Live fares for MDW → BOS are updating. Use the search below for real-time prices.
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Updated daily
Flight time
2h 15m
Nonstop, typical
Distance
858 mi
MDW → BOS
Cheapest month
November 2026
Fares from $97
Nonstop airlines
1
Southwest Airlines
Nonstop flights from Chicago to Boston
Want to skip the layover? Nonstops from Chicago to Boston are flown by Southwest Airlines, getting you there in about 2h 15m. For the lowest fares, book around 3–6 weeks before departure — last-minute nonstops on this route rarely come cheap.
Booking insights: Chicago → Boston
- Distance: 858 miles · nonstop flight time: 2h 15m.
- Cheapest upcoming week in the live data starts around Nov 12, with fares from $97.
- Of the months we're tracking right now, November 2026 has the lowest fares, starting at $97.
- Rule of thumb for this route: the sweet spot is usually 3–6 weeks before departure.
- Midweek departures (Tue–Thu) are consistently cheaper than weekend flights.
- Set a free Airfare Deal alert instead of checking daily — the best fares can sell out in hours.
Price trend
Cheapest departure weeks ahead
Departing around Nov 12 is currently the cheapest window — about $178 less than the nearest weeks. Based on recent fares found for this route; prices change quickly.
Cheapest month · Chicago → Boston
November 2026
Every date's recent round-trip fare, at a glance.
Fares from
$97
Cheapest: Sat, Nov 14 — $97 · Priciest: Nov 15 — $182
Get this fare →Recent fares found for specific dates in November 2026. Blank days had no recent fare in our data — ask our team and we'll check them for you.
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Flying from Chicago to Boston: what you need to know
The flight
Chicago to Boston covers 858 miles, and a nonstop gets it done in about 2h 15m. That's long enough to settle in with a coffee and a downloaded show, short enough that a connection rarely makes sense — a layover usually doubles your travel day to save very little.
Airlines on this route
Southwest Airlines flies this route nonstop. That matters more than it sounds: the cheapest fare on one carrier is rarely the same product as the cheapest on another. Checked-bag fees, free seat selection and change rules all differ, so compare the full trip cost before you pick a winner. See our airline guides for exactly what each carrier charges — then send an enquiry and we'll confirm the all-in price for your dates.
Leaving from Chicago (MDW)
Plan to be at the airport two hours before a domestic departure — ninety minutes can work at smaller airports outside peak times, but security lines are the one variable you can't control. If you're checking a bag, add time rather than cutting it close. Our Chicago airport guide covers terminals, parking and ground transport so you can plan the trip to the airport, not just the flight.
Arriving in Boston (BOS)
Before you land, know how you're getting from the airport to where you're staying — it's the part of the trip people forget to plan. The Boston airport guide lays out your ground options, from transit and shuttles to rideshares and rental cars. Flying back the other way? Check Boston to Chicago fares — prices on the return direction often move on a different rhythm.
When to book
Of the months we're currently tracking, November 2026 is coming in cheapest for this route, with fares from $97. As a rule, booking 3–6 weeks ahead lands you in the sweet spot — leave it to the final two weeks and prices usually climb. If you see a fare that works, don't wait around: set a fare alert on this page and we'll watch the price for you.
Good to know before you go
- Nonstop time on this route is about 2h 15m — a one-stop itinerary needs to be a lot cheaper to be worth the extra hours.
- Tuesday and Wednesday departures are typically the cheapest days on domestic routes.
- Screenshot your fare before you enquire — prices move, and a saved fare helps our team match or beat it.
- November 2026 is currently the cheapest tracked month on this route — check those dates first if you're flexible.
- Morning flights are delayed less often than evening ones — earlier departures have the best on-time record.
Chicago to Boston flight FAQs
How long is the flight from MDW to BOS?
Nonstop flights from Chicago to Boston take about 2h 15m and cover roughly 858 miles. One-stop itineraries add 2–4 hours depending on the layover city.
Are there nonstop flights from Chicago to Boston?
Yes — look for Southwest Airlines on this route. Nonstop seats are usually priced best 3–6 weeks before departure.
What is the cheapest month to fly from Chicago to Boston?
Of the months we're tracking right now, November 2026 has the lowest fares from Chicago to Boston, starting at $97. Fares update as new data comes in, so it's worth setting a free alert for your dates.
How much are last minute flights from MDW to BOS?
Last-minute flights from MDW to BOS (booked within 7 days of departure) typically cost noticeably more than fares booked 3–6 weeks out. Booking early is the smarter move.
What is a good round-trip deal from Chicago to Boston?
A good deal is anything at or below the recent fares shown above. Set a free Airfare Deal alert and we'll ping you the moment fares drop.
Which airlines fly from Chicago to Boston?
The main carriers on this route are Southwest Airlines. Comparing all of them on the live search below usually surfaces the lowest fare for your dates.
How early should I get to Chicago airport for this flight?
Plan on two hours before departure for a domestic flight — ninety minutes can work at smaller airports outside peak times. If you're checking a bag, earlier is better; the bag-drop line, not the flight, is what runs late.
Do the cheapest fares on this route include a checked bag?
Usually not. Basic economy fares on most airlines include a carry-on but charge extra for checked bags, and seat selection can cost more too. Add up the real total before comparing — a slightly higher regular fare sometimes works out cheaper. Our team confirms the full breakdown with you before you pay.
More cheap flights from Chicago
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