CHI - BIL

$151 Find Cheap Flights from Chicago to Billings

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Billings departing on 7/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Billings

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Billings, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Billings, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$271
Delta
Sat 7/4Sat 7/11
MDW - BIL • 1 stop
Cheapest non-stop
$372
American Airlines
Sat 8/22Mon 8/31
ORD - BIL • Non-stop
Top airlines
Cheapest • from $271 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 3h 23m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 84% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $290 (round-trip)
Shortest trip • 5h 27m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 15% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Billings!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Billings (CHI-BIL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Billings that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Billings

Sat, Jul 4 - Sat, Jul 11
Delta Logo
1:49 pm - 8:02 pm
MDW
-
BIL
7h 13m
1 stop
Delta Logo
6:24 am - 1:09 pm
BIL
-
MDW
5h 45m
1 stop
$271Delta
Sat, Jul 4 - Sat, Jul 11
Delta Logo
5:00 pm - 10:51 pm
ORD
-
BIL
6h 51m
1 stop
Delta Logo
6:24 am - 11:45 am
BIL
-
ORD
4h 21m
1 stop
$271Delta
Sat, Aug 22 - Sat, Aug 29
Delta Logo
12:29 pm - 10:53 pm
ORD
-
BIL
11h 24m
2 stops
Delta Logo
5:20 am - 11:59 am
BIL
-
ORD
5h 39m
1 stop
$276Delta
Sat, Aug 22 - Sat, Aug 29
Delta Logo
12:29 pm - 10:53 pm
ORD
-
BIL
11h 24m
2 stops
Delta Logo
5:20 am - 4:17 pm
BIL
-
ORD
9h 57m
2 stops
$281Delta
Sat, Jul 4 - Sat, Jul 11
Delta Logo
1:49 pm - 8:02 pm
MDW
-
BIL
7h 13m
1 stop
Delta Logo
6:24 am - 1:09 pm
BIL
-
MDW
5h 45m
1 stop
$291Delta
Sat, Jul 4 - Sat, Jul 11
Delta Logo
5:00 pm - 10:51 pm
ORD
-
BIL
6h 51m
1 stop
Delta Logo
6:24 am - 11:45 am
BIL
-
ORD
4h 21m
1 stop
$291Delta
Sat, Jul 4 - Sat, Jul 11
Delta Logo
10:55 am - 8:02 pm
MDW
-
BIL
10h 07m
2 stops
Delta Logo
6:24 am - 1:09 pm
BIL
-
MDW
5h 45m
1 stop
$296Delta
Sat, Jul 4 - Sat, Jul 11
Delta Logo
9:48 am - 8:02 pm
ORD
-
BIL
11h 14m
2 stops
Delta Logo
5:20 am - 12:00 pm
BIL
-
ORD
5h 40m
1 stop
$296Delta
Mon, Aug 17 - Sat, Aug 22
Delta Logo
5:57 pm - 11:30 pm
ORD
-
BIL
6h 33m
1 stop
Delta Logo
5:20 am - 11:59 am
BIL
-
ORD
5h 39m
1 stop
$302Delta
Fri, Sep 4 - Fri, Sep 11
American Airlines Logo
3:54 pm - 10:47 pm
ORD
-
BIL
7h 53m
1 stop
American Airlines Logo
12:28 pm - 4:30 pm
BIL
-
ORD
3h 02mnonstop
$323American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Billings flights

Get data-powered insights and trends into flights from Chicago to Billings to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Billings?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Billings departing in July.

What is the cheapest Chicago to Billings flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Billings costs $300 on the route between Chicago O'Hare Intl Airport (ORD) and Billings (BIL). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Billings?

The average price of all round-trip flights from Chicago to Billings clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Billings, you should consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Mondays.

What is the cheapest month to fly from Chicago to Billings?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Billings, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Billings is March, where tickets cost $208 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $283 and $275 respectively.

Can I save money by flying with a layover from Chicago to Billings?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $499, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$151
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport to Billings

When to book flights from Chicago to Billings

Are your dates flexible? Find out the best times to travel from Chicago to Billings based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Billings

  • What is the cheapest flight from Chicago to Billings?

    In the last 5 days, the lowest price for a flight from Chicago to Billings was $151 for a one-way ticket and $271 for a round-trip.

  • Do I need a passport to fly between Chicago and Billings?

    A passport is not required to fly from Chicago to Billings.

  • Which airports will I be using when flying from Chicago to Billings?

    On your way to Billings, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Billings Logan Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Billings?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Billings flight route.

  • Which aircraft models fly most regularly from Chicago to Billings?

    The Embraer 175 is the aircraft model that flies most regularly on the Chicago to Billings flight route.

  • Which airline alliances offer flights from Chicago to Billings?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Billings, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Billings?

    There are nonstop flights from Chicago to Billings on a daily basis.

  • Which is the best airline for flights from Chicago to Billings, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Billings are Delta and United Airlines. With an average price for the route of $258 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $369 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Billings?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Billings.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Billings?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Billings from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Billings?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Billings with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Billings?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Billings from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Billings

  • Looking for a cheap flight? 25% of our users found flights on this route for $541 or less round-trip.

Prefer to fly direct from Chicago to Billings?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Billings Logan Intl.
Find which airlines fly direct from Chicago to Billings Logan Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago to Billings Logan Intl

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

Billings Logan Intl to Chicago

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Reviews of the top 3 airlines serving from Chicago to Billings

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Billings. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Billings? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8395 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
7.8Comfort
Airline reviews

Connection flights should be spaced out farther because too close I missed my connection.

8.0 ExcellentAnonymous, Jun 2026
PHL - ATL
Read more Delta reviews

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Everything you need to know for your flight from Chicago to Billings

Information on your arrival and departure airports