Domestic route
Cheap flights from Boston to Chicago
Boston Logan International Airport (BOS) to O'Hare International Airport (ORD). 864 miles, 2h 10m nonstop.
BOS to ORD at a glance
Computed from airline schedules and the fares we track for this route. Refreshed several times a day.
- Distance
- 864 milesgreat-circle
- Typical flight time
- 2h 10mnonstop, gate to gate
- Nonstop airlines
- AADLUAB66 airlinesAmerican, Delta, United
- Nonstop flights per day
- 32all airlines combined
- Cheapest month
- January 2027over the next six months
- Best day to fly
- Tuesday17% less than Friday
- Time difference
- 1h behindChicago vs Boston
Boston to Chicago
Round trips from $68
Per traveler, taxes and fees included. Lowest fare we found departs Tue, Jan 5.
Cheapest month: January 2027
See fares on these datesLock any fare free — pay only when you accept your last-minute deal
Or ask an agent on WhatsAppBoston to Chicago fares by month
Lowest round-trip economy fare per traveler in each of the next six months, taxes and fees included. Select a month to search that date.
Airlines flying Boston to Chicago
6 airlines fly nonstop with 32 departures a day combined, plus 3 more with one stop.
- AAAmerican AirlinesoneworldNonstop · 7 flights a day · first checked bag from $40
- DLDelta Air LinesSkyTeamNonstop · 7 flights a day · first checked bag from $35
- B6JetBlueNonstop · 7 flights a day · first checked bag from $40
- UAUnited AirlinesStar AllianceNonstop · 7 flights a day · first checked bag from $40
- NKSpirit AirlinesLow-costNonstop · 2 flights a day · first checked bag from $55
- SYSun Country AirlinesLow-costNonstop · 2 flights a day · first checked bag from $45
- MXBreeze AirwaysLow-costConnecting via RDU, ORF · first checked bag from $45
- F9Frontier AirlinesLow-costConnecting via PHL, CLE · first checked bag from $55
- WNSouthwest AirlinesLow-costConnecting via BWI, BNA, STL · first checked bag from $35
Connecting options
Hubs where one airline can carry you on both legs, most choices first.
- Baltimore (BWI)WN1 airline
- Nashville (BNA)WN1 airline
- St. Louis (STL)WN1 airline
- Philadelphia (PHL)F91 airline
- Cleveland (CLE)F91 airline
Which airport should I use?
BostonChicago has 2 airports. Fares can differ by $50 to $150 round trip between them, so check the alternatives before you book.
Other arrival airports near Chicago
Tips for this route
- American, Delta, United and JetBlue all fly BOS to ORD nonstop, so compare the total with bags before picking the lowest base fare: the difference between a basic and a standard economy ticket is often less than one checked bag each way.
- January 2027 is the cheapest month to fly over the next six months, with round trips from $68; September 2026 is the most expensive at $92 and up, a difference of $24 per traveler.
- Departing on a Tuesday averages 17% less than a Friday on this route. If your dates are flexible, shift the outbound by a day or two and check the calendar view before you book.
- Fares on this route are usually lowest 4 to 8 weeks before departure and rise sharply inside two weeks.
Destination guide
Chicago: Big-shoulders architecture and a lakefront for everyone
Chicago is America's most connected inland hub — O'Hare and Midway between them have nonstops from nearly every US city — so fares are consistently reasonable. The lakefront, the architecture and the food make it a strong long weekend.
Best time to visit: June–September is warm, with festivals almost every weekend (and the highest hotel rates). May and October are cool and cheaper; winter is cold but hotels are a bargain.
Flying the other way? Chicago to BostonFares, airlines and tips for ORD to BOS.Ready to compare live fares?
See every airline on BOS–ORD side by side with bags and seat rules spelled out.
Search Boston to ChicagoBoston to Chicago: common questions
How long is the flight from Boston to Chicago?
A nonstop flight from Boston (BOS) to Chicago (ORD) takes about 2h 10m gate to gate, covering 864 miles. Connecting itineraries add the layover, typically 1 to 3 hours more in total.
Which airlines fly nonstop from BOS to ORD?
American Airlines, Delta Air Lines, United Airlines, JetBlue, Spirit Airlines and Sun Country Airlines operate nonstop flights from Boston (BOS) to Chicago (ORD), with 32 nonstop departures a day between them. One-stop options connect through BWI, BNA and STL.
What is the cheapest month to fly from Boston to Chicago?
Over the next six months, January 2027 has the lowest round-trip fares from Boston (BOS) to Chicago (ORD), starting at $68 per traveler including taxes and fees. Within any month, Tuesday departures average the lowest prices.
How far in advance should I book Boston to Chicago flights?
Fares on this route are usually lowest 4 to 8 weeks before departure and rise sharply inside two weeks. Air1 Tickets includes free cancellation within 24 hours of booking on every fare, so you can lock in a good price and keep looking.
What is the time difference between Boston and Chicago?
Chicago is 1 hour behind Boston. BOS is on America/New York time and ORD on America/Chicago time. Departure and arrival times in search results are always shown in local time at each airport.
Related routes
Other popular city pairs from the same departure city and to the same destination, with the lowest round-trip fares we found.