$149 Cheap Flights from Chicago (ORD) to Billings (BIL)

View $149 flight on Sat, Nov 8, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Billings Logan Intl. Airport (BIL)

Cheap Flights from Chicago to Billings (ORD-BIL)

Prices were available within the past 7 days and start at $149 for one-way flights and $229 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Sep 27 - Sat, Oct 4
ORD
Chicago
BIL
Billings
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 27 from Chicago to Billings, returning Sat, Oct 4, priced at $229 found 3 days ago
American Airlines
Wed, Oct 15 - Sun, Oct 19
ORD
Chicago
BIL
Billings
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 15 from Chicago to Billings, returning Sun, Oct 19, priced at $229 found 1 day ago
United
Tue, Sep 30 - Sun, Oct 5
ORD
Chicago
BIL
Billings
$229 Roundtrip, found 10 hours ago
$229
Roundtrip
found 10 hours ago
Select United flight, departing Tue, Sep 30 from Chicago to Billings, returning Sun, Oct 5, priced at $229 found 10 hours ago
Delta
Tue, Sep 30 - Sat, Oct 4
ORD
Chicago
BIL
Billings
$234 Roundtrip, found 3 days ago
$234
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 30 from Chicago to Billings, returning Sat, Oct 4, priced at $234 found 3 days ago
United
Wed, Oct 22 - Tue, Oct 28
ORD
Chicago
BIL
Billings
$239 Roundtrip, found 3 hours ago
$239
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Oct 22 from Chicago to Billings, returning Tue, Oct 28, priced at $239 found 3 hours ago
United
Sat, Sep 13 - Sat, Sep 20
ORD
Chicago
BIL
Billings
$244 Roundtrip, found 16 hours ago
$244
Roundtrip
found 16 hours ago
Select United flight, departing Sat, Sep 13 from Chicago to Billings, returning Sat, Sep 20, priced at $244 found 16 hours ago
United
Wed, Oct 22 - Tue, Oct 28
ORD
Chicago
BIL
Billings
$249 Roundtrip, found 3 hours ago
$249
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Oct 22 from Chicago to Billings, returning Tue, Oct 28, priced at $249 found 3 hours ago
American Airlines
Wed, Oct 22 - Tue, Oct 28
ORD
Chicago
BIL
Billings
$249 Roundtrip, found 3 hours ago
$249
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Oct 22 from Chicago to Billings, returning Tue, Oct 28, priced at $249 found 3 hours ago
Delta
Sat, Nov 22 - Thu, Nov 27
ORD
Chicago
BIL
Billings
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 22 from Chicago to Billings, returning Thu, Nov 27, priced at $254 found 1 day ago
Hawaiian Airlines
Wed, Dec 3 - Tue, Dec 9
ORD
Chicago
BIL
Billings
$334 Roundtrip, found 5 days ago
$334
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Wed, Dec 3 from Chicago to Billings, returning Tue, Dec 9, priced at $334 found 5 days ago

Find the cheapest month to fly from Chicago (ORD) to Billings (BIL)

August is typically the cheapest month to fly

From $209 - $523 per traveler.

Graph displaying average flight prices per month

Alternative airports near Billings

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Logan Intl. BIL. Cheapest and Closest option available. Average driving time to city center is 5 minutes. Flights from $466
BIL
Logan Intl.
CheapestClosest
Average driving time to city center5 min
Flights from $466
Flights from Chicago (ORD) to Billings (BIL)
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Hawaiian Airlines, United
Roundtrip price
$228
Distance
1057 mi
Average flight time
2 hours 11 mins

Chicago to Billings Flights

The cheapest times to fly from Chicago to Billings

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Billings are during the month of September. You can find some of the cheapest flights from Chicago to Billings with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Billings

Sunday is one of the best days to book for cheap flights from Chicago to Billings: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Billings

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Billings in 2025. You can also book with separate airlines for your outbound and return journeys, from $149 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Billings flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Billings airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL) cost?
Lock in a cheap one-way flight from $149 or cheap return flight from $229 from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL)?
September is the cheapest month to fly from ORD to BIL. Traveling during an off-peak travel window is often the key to scoring lower fares.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll fly you from ORD to BIL. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
How many flights per day from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL)?
Direct flights from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to BIL?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from ORD to BIL?
American Airlines has the strongest track record for on-time direct flights from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL), with an on-time rating of 87%. Use the Expedia App to check your flight schedule before you leave and get real-time updates about any trip changes.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL)?
To arrive at Logan Intl. Airport (BIL) without delays, choose a flight that takes off from O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL) last-minute?
Holding off until just before your departure to book your flight from ORD to BIL generally means paying more. While you may find some last-minute offers, they're not always guaranteed. Keep your travel schedule open to maximize your chances of scoring a bargain.
Is it cheaper to book an ORD to BIL flight and hotel package?
Securing an ORD to BIL flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Select from our impressive range of accommodations and then add flights, activities and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BIL)?
If you booked your ORD to BIL flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

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*Available to One Key members.