$49 Cheap flights from Logan Intl. to O'Hare Intl. (BOS to ORD)

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

Compare Flight Prices from Boston to Chicago

Affordable Airfare Tickets from BOS to ORD Airport

The cheapest flights to O'Hare Intl. found within the past 7 days were $109 round trip and $49 one way. Prices and availability subject to change. Additional terms may apply.

Wed, May 21 - Wed, May 28
BOS
Boston
ORD
Chicago
$109 Roundtrip, found 7 hours ago
$109
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Wed, May 21 from Boston to Chicago, returning Wed, May 28, priced at $109 found 7 hours ago
Thu, Oct 23 - Thu, Oct 30
BOS
Boston
ORD
Chicago
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Oct 23 from Boston to Chicago, returning Thu, Oct 30, priced at $109 just found
Mon, Sep 22 - Mon, Sep 22
BOS
Boston
ORD
Chicago
$112 Roundtrip, found 4 hours ago
$112
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Mon, Sep 22 from Boston to Chicago, returning Mon, Sep 22, priced at $112 found 4 hours ago
Tue, May 6 - Tue, May 6
BOS
Boston
ORD
Chicago
$113 Roundtrip, found 6 hours ago
$113
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Tue, May 6 from Boston to Chicago, returning Tue, May 6, priced at $113 found 6 hours ago
Tue, May 13 - Tue, May 13
BOS
Boston
ORD
Chicago
$114 Roundtrip, found 2 hours ago
$114
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, May 13 from Boston to Chicago, returning Tue, May 13, priced at $114 found 2 hours ago
Thu, Oct 23 - Thu, Oct 30
BOS
Boston
ORD
Chicago
$114 Roundtrip, just found
$114
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Oct 23 from Boston to Chicago, returning Thu, Oct 30, priced at $114 just found
Tue, May 6 - Wed, May 7
BOS
Boston
ORD
Chicago
$117 Roundtrip, found 6 hours ago
$117
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, May 6 from Boston to Chicago, returning Wed, May 7, priced at $117 found 6 hours ago
Mon, May 5 - Thu, May 8
BOS
Boston
ORD
Chicago
$118 Roundtrip, just found
$118
Roundtrip
just found
Select JetBlue Airways flight, departing Mon, May 5 from Boston to Chicago, returning Thu, May 8, priced at $118 just found
Thu, Jun 5 - Sat, Jun 7
BOS
Boston
ORD
Chicago
$119 Roundtrip, just found
$119
Roundtrip
just found
Select United flight, departing Thu, Jun 5 from Boston to Chicago, returning Sat, Jun 7, priced at $119 just found
Wed, Sep 17 - Wed, Sep 24
BOS
Boston
ORD
Chicago
$120 Roundtrip, found 3 hours ago
$120
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Wed, Sep 17 from Boston to Chicago, returning Wed, Sep 24, priced at $120 found 3 hours ago

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

Price found within the past 48 hours. Click for updated prices.
Quality Inn

Quality Inn

2.5 out of 5
per person
Jun 20 - Jun 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Rockford (RFD)
Baymont by Wyndham Portage Indiana Dunes

Baymont by Wyndham Portage Indiana Dunes

2.5 out of 5
per person
Jun 20 - Jun 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Days Inn and Suites by Wyndham Hammond, IN

Days Inn and Suites by Wyndham Hammond, IN

2 out of 5
per person
Jun 20 - Jun 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Baymont by Wyndham Gurnee

Baymont by Wyndham Gurnee

2.5 out of 5
per person
Jun 20 - Jun 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Quality Inn Monee I-57

Quality Inn Monee I-57

2.5 out of 5
per person
Jun 20 - Jun 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (MDW)
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Frequently asked questions

Are there direct flights from Logan Intl. Airport to ORD?
Your next unforgettable adventure is on the other side of just one flight. You can jet direct from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD) with multiple airlines, including United Airlines and American Airlines.
How long is the flight from Logan Intl. Airport to O'Hare Airport?
If you were hoping to get some decent shut-eye during your Boston to Chicago flight, you may have to think again. The normal flight time between Logan Intl. Airport (BOS) and O’Hare Intl. Airport (ORD) is a quick 2 hours and 56 minutes — just enough to get comfortable and rest your eyes for a little while.
What is the flight distance from BOS to O'Hare Airport?
With a mere 860 mi separating BOS and ORD, there’ll be little time between the seat belt sign turning off and the captain readying the wheels for touchdown.
What airlines fly from BOS to ORD?
With a range of airlines operating direct flights from BOS to O’Hare Intl. Airport (ORD), you’re spoiled for choice. Here are some of the most well-known air carriers:

  • United Airlines - (UA) with 208 flights every month
  • American Airlines - (AA) with 195 flights every month
  • Delta - (DL) with 147 flights every month
  • JetBlue - (B6) with 56 flights every month

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 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that 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 2021, 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 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Flight information from Boston to Chicago

 

Traveling From
Logan Intl.
Traveling To
O'Hare Intl.
Shortest Flight Time
0 hours 55 mins
Earliest Departure Time
5:00AM CDT
Latest Departure Time
8:59PM CDT
Lowest Flight Price
$109

Route Info

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


Origin:
BOS - Logan International Airport
Destination:
ORD - 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 20 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 $109 and $120. 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) 55 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, May 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.