$49 Cheap Flights from Boston to Chicago

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly from Logan Intl. to O'Hare Intl.

Amazing BOS to ORD Flight Deals

The cheapest flights to O'Hare Intl. found within the past 7 days were $91 round trip and $49 one way. Prices and availability subject to change. Additional terms may apply.

Flight Schedule for BOS to ORD

CarrierFlightDepart BOSArrive ORDSun
11/28
Mon
11/29
Tue
11/30
Wed
12/1
Thu
12/2
Fri
12/3
Sat
12/4
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AA226505:03 am07:06 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA127506:15 am08:09 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL570806:50 am08:52 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA150907:30 am09:39 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA27309:50 am11:42 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA358709:53 am00:00 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL241310:20 am00:15 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA156411:20 am01:12 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA62900:15 pm02:18 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA463601:30 pm03:36 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL560202:19 pm04:15 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA226904:15 pm06:27 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA233504:45 pm06:37 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL139705:00 pm07:04 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA410605:45 pm07:55 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA33606:21 pm08:15 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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B6271107:00 pm09:01 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA464807:50 pm09:55 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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DL583107:50 pm09:48 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA124208:25 pm10:27 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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UA60109:33 pm11:28 pmCheck Fare
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B631109:30 am11:31 am
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UA74806:15 am08:09 am
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UA31704:45 pm06:38 pm
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Best O'Hare Intl. Flight and Hotel Packages

O'Hare Intl. flight + hotel packages - economy flights

Trump International Hotel & Tower Chicago
theWit Chicago - a DoubleTree by Hilton Hotel
Residence Inn Chicago Downtown/Loop
The Langham, Chicago
Thompson Chicago
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FAQs about flights from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD)

Can I catch a flight from Boston, MA Airport (BOS-Logan Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.) right now?

Ensure you go to the Covid-19 Travel Advisor to discover if there are any current quarantine requirements and travel advice reports in effect in Chicago, IL Airport (ORD-O'Hare Intl.) when flying from Boston, MA Airport (BOS-Logan Intl.).

Are there direct flights from Logan Intl. Airport (BOS) to Chicago, IL Airport (ORD-O'Hare Intl.)?

Sometimes, it's the journey that counts; other times, the magic is in the destination. But if you just want to get to where you're going fast, multiple airlines offer direct flights from Logan Intl. Airport to O'Hare Intl. Airport (ORD), including American Airlines and United Airlines.

If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to O'Hare Intl. Airport (ORD), please visit our Customer Service Portal.

How long is the flight from Logan Intl. Airport (BOS) to ORD?

Flying from Logan Intl. Airport (BOS) to ORD is a breeze as the flight usually lasts 2 hours and 51 minutes. With so little time in the air, there's a good chance you'll exit the plane feeling as fresh as when you got on.

What is the flight distance from BOS to O'Hare Airport?

From Logan Intl. Airport, you'll cover 870 mi before arriving at O'Hare Intl. Airport (ORD). That should be enough time to finish a few chapters of your book and perhaps even manage forty winks.

What airlines fly from Boston, MA Airport (BOS-Logan Intl.) to O'Hare Intl. Airport (ORD)?

If you want to fly direct from BOS to ORD, you've got quite a few options. Below are the leading airlines that will get you to Chicago without any fuss:

  • American Airlines - (AA) with 202 flights every month
  • United Airlines - (UA) with 110 flights every month
  • Delta - (DL) with 145 flights every month
  • JetBlue - (B6) with 49 flights every month
What airlines have practices regarding COVID-19 in place and use social distancing?

From the moment you enter the departure terminal to when you leave the arrivals terminal, if you're flying with United Airlines, American Airlines or Delta you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.

What is the best day to buy a plane ticket?

This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2020. Wednesday and Friday prices are also good, but you may want to prepare your budget if booking on a Sunday, as data shows the end of the week is when prices are generally at their highest.

What are the cheapest days to fly?

Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2020, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.

How far in advance can you book a flight?

Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2020 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2 weeks to 2 months prior to their travel dates.

How can I save money on airline tickets?

We'll let you in on a secret...You can save big on flights if you mix and match your airlines and fare types. In fact, travelers who booked flights on Travelocity in 2020 saved nearly 40% when their return flights consisted of two different airlines or fare types.

*According to flight demand on Travelocity.com from January to December 2020. Savings are subject to change based on departure location, date and destination.

Logan Intl. to O'Hare Intl. Flight FAQ

Traveling From Logan Intl.
Traveling To O'Hare Intl.
Shortest Flight Time 0 hours 50 mins
Earliest Departure Time 5:00AM CST
Latest Departure Time 6:55PM CST
Lowest Flight Price $91

Route Info

Flight path for flights from Logan International Airport to O'Hare International Airport

Distance:
869.00 miles

Airlines & Aircraft Used on BOS to ORD Flight Routes

Airline Carrier
Aircraft
American Airlines
Airbus A320-100/200
American Airlines
Airbus A320-100/200
American Airlines
Airbus A320-100/200
American Airlines
Beechcraft 1900/1900C/1900D
Delta Air Lines
Airbus A319
Delta Air Lines
Airbus A320-100/200
Delta Air Lines
Airbus A320-100/200
Delta Air Lines
Airbus A321-100/200
Delta Air Lines
Boeing 737-200 pax
Delta Air Lines
Boeing 737-300 pax
Delta Air Lines
Boeing 737-700 (winglets) pax
Delta Air Lines
Boeing 757 all pax models
Jet Airways (India)
Embraer RJ145 Amazon
JetBlue Airways
Airbus A319
JetBlue Airways
Airbus A330-300
JetBlue Airways
Boeing 737-700 pax
JetBlue Airways
Boeing 737-800 pax

Discover our best flights from Boston BOS to Chicago ORD. 

With 17 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Boston BOS to Chicago ORD at the right price  

Airfares to Chicago ORD from Boston BOS currently cost between $91 and $115. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Boston BOS to Chicago ORD 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Boston BOS to Chicago ORD on Travelocity starting at $49. Prices and availability subject to change. Additional terms may apply. 

 

Get to Chicago ORD from Boston BOS quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to ORD from BOS to take around 0 hour(s) 50 min(s).  

 

Find our cheapest airfares for flights from Boston BOS to Chicago ORD

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to ORD from BOS. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Boston BOS to Chicago ORD today 

If you’re flexible about when you travel, December is usually the cheapest month to fly from Boston BOS to Chicago ORD. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Chicago ORD from Boston BOS 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to ORD from BOS have this option.  

 

Travel with confidence when you book flights to Chicago ORD from Boston BOS with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.