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$156+ Cheap flights from Columbia, MO (COU) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
COU — CHI
Jul 27 — Aug 31
Mon 7/27
Mon 8/3
1 adult, Economy
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Cheap flight deals from Columbia to Chicago

Cheapest flights from Columbia to Chicago
Explore the most affordable flight options available from Columbia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 27, 2026.

This American Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:43 pm
COU
-
ORD
Nonstop1h 36m
American Airlines
Sun 9/67:49 pm
ORD
-
COU
Nonstop1h 30m
American Airlines
Deal found 6/24$239
This American Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:20 am
COU
-
ORD
Nonstop1h 41m
American Airlines
Sun 7/198:29 am
ORD
-
COU
Nonstop1h 32m
American Airlines
Deal found 6/25$241
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:15 am
COU
-
ORD
Nonstop1h 38m
United Airlines
Sun 10/119:00 am
ORD
-
COU
Nonstop1h 37m
United Airlines
Deal found 6/25$251
This American Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:32 pm
COU
-
ORD
Nonstop1h 51m
American Airlines
Sat 7/257:43 pm
ORD
-
COU
Nonstop1h 32m
American Airlines
Deal found 6/24$254
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/103:25 pm
COU
-
ORD
Nonstop1h 40m
United Airlines
Sun 7/128:40 am
ORD
-
COU
Nonstop1h 33m
United Airlines
Deal found 6/23$269
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:15 am
COU
-
ORD
Nonstop1h 38m
United Airlines
Sun 10/189:00 am
ORD
-
COU
Nonstop1h 37m
United Airlines
Deal found 6/22$287
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/110:49 am
COU
-
ORD
Nonstop1h 41m
United Airlines
Thu 7/98:40 am
ORD
-
COU
Nonstop1h 33m
United Airlines
Deal found 6/23$299
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:00 am
COU
-
ORD
Nonstop1h 40m
United Airlines
Sun 8/910:00 pm
ORD
-
COU
Nonstop1h 33m
United Airlines
Deal found 6/25$309
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:00 am
COU
-
ORD
Nonstop1h 40m
United Airlines
Sun 7/1910:00 pm
ORD
-
COU
Nonstop1h 33m
United Airlines
Deal found 6/25$323
This United Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1310:49 am
COU
-
ORD
Nonstop1h 41m
United Airlines
Tue 7/218:40 am
ORD
-
COU
Nonstop1h 33m
United Airlines
Deal found 6/24$324
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1012:43 pm
COU
-
ORD
Nonstop1h 36m
American Airlines
Thu 8/137:49 pm
ORD
-
COU
Nonstop1h 30m
American Airlines
Deal found 6/23$327
This American Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
COU
-
ORD
Nonstop1h 38m
American Airlines
Mon 7/67:29 pm
ORD
-
COU
Nonstop1h 32m
American Airlines
Deal found 6/24$329

Find flight deals from Columbia to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Columbia (COU) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(American Airlines)

One-way from

$156
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$308

Good round-trip deal

$328 or less

Good one-way deal

$294 or less
Provider with most accurate pricing for Columbia Regional-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Columbia Regional-Chicago (CHI) flights.
Search Deals
From Columbia Regional to Chicago (CHI)
Search Deals
One-way flight from Columbia Regional to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Columbia Regional to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Columbia Regional to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Columbia to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 27, 2026.
Use the filters below to find and compare flights from Columbia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Tue 8/11

6:15 am-7:54 am

Nonstop1h 39m

Chicago O'Hare Intl

Sat 8/15

9:20 pm-10:55 pm

Nonstop1h 35m

$309

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Wed 9/9

11:20 am-1:03 pm

Nonstop1h 43m

Chicago O'Hare Intl

Sat 9/12

8:59 am-10:38 am

Nonstop1h 39m

$309

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Thu 8/6

8:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Fri 8/14

12:50 pm-2:30 pm

Nonstop1h 40m

$309

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Wed 8/26

6:15 am-7:54 am

Nonstop1h 39m

Chicago O'Hare Intl

Sun 8/30

9:20 pm-10:55 pm

Nonstop1h 35m

$309

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Sat 7/11

3:25 pm-5:05 pm

Nonstop1h 40m

Chicago O'Hare Intl

Wed 7/15

1:15 pm-2:50 pm

Nonstop1h 35m

$339
Quickest round-trip

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Thu 7/30

8:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Mon 8/3

8:40 am-10:13 am

Nonstop1h 33m

$369

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Wed 7/8

10:49 am-12:30 pm

Nonstop1h 41m

Chicago O'Hare Intl

Sun 7/12

10:00 pm-11:33 pm

Nonstop1h 33m

$369

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Thu 9/3

6:15 am-7:54 am

Nonstop1h 39m

Chicago O'Hare Intl

Sun 9/6

8:50 am-8:59 pm

2 stops12h 09m

$467

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Thu 8/27

3:12 pm-5:00 pm

Nonstop1h 48m

Chicago O'Hare Intl

Fri 8/28

12:50 pm-2:30 pm

Nonstop1h 40m

$477

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Tue 7/21

10:49 am-12:30 pm

Nonstop1h 41m

Chicago O'Hare Intl

Thu 7/23

1:15 pm-2:50 pm

Nonstop1h 35m

$477

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/26

Showing 1-10 of 24 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Columbia to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Columbia to Chicago in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Columbia, Missouri-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Columbia, Missouri-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Columbia, Missouri-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Columbia, Missouri-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Columbia, Missouri-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Columbia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Columbia with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Columbia to Chicago

What is the cheapest month to book a flight from Columbia, Missouri to Chicago?

Currently, November is the cheapest month in which you can book a flight from Columbia, Missouri to Chicago (average of $99). Flying from Columbia, Missouri to Chicago in July is currently the most expensive (average of $238). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from COU to CHI?

Find hourly flight availability from Columbia to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 27, 2026.

When flying from Columbia, Missouri to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 9% versus a flight at noon.

Weekly flight availability from Columbia, Missouri to Chicago

Explore weekly flight availability from Columbia to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 27, 2026.

The most flights from COU to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Columbia, Missouri to Chicago?

How far ahead should I book a flight from Columbia, Missouri to Chicago?

The best time to book flights from Columbia, Missouri to Chicago is 40 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest day to fly from Columbia, Missouri to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Columbia to Chicago. Price data was last updated on June 20, 2026.

Travelers seeking maximum savings on their Columbia, Missouri to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 27, 2026.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Columbia to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,896 reviews

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
9,896 reviews
United Airlines
7.4
Good
9,896 reviews

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.1
Good
11,779 reviews
United Airlines
7.4
Good
9,896 reviews

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Columbia to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Columbia to Chicago?

    Most people fly from Columbia Regional (COU) if they book a flight from Columbia to Chicago. On average, Columbia Regional has 8 outbound flights to Chicago per day from 2 airlines. Columbia Regional is conveniently located just 11.1 mi from Columbia’s city center.

  • How long is the flight from Columbia, Missouri to Chicago?

    For as low as $287, United Airlines can have you in Chicago from Columbia, Missouri in 1h 38m. Columbia, Missouri and Chicago are separated by a distance of 315 mi. All flights are typically nonstop.

  • What are the cheapest airlines flying from Columbia, Missouri to Chicago round-trip?

    According to our current data, American Airlines ($179), and United Airlines ($179) offers the cheapest pricing from Columbia, Missouri to Chicago. American Airlines is currently priced 30% below the average price you’ll pay for this route.

  • What are the most reliable airlines from Columbia, Missouri to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Columbia, Missouri to Chicago on time: American Airlines (80%), Envoy Air (80%), Qatar Airways (79%).

  • What are the cheapest flights from Columbia, Missouri to Chicago?

    The cheapest flight price from Columbia, Missouri to Chicago is $163. On average you can expect to pay $595. The most popular route, (Columbia Regional - Chicago O'Hare Intl), can usually be booked for $239.

  • Can I find deals for flights from Columbia to Chicago that include hotel bookings?

    Yes. In addition to deals on Columbia to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Columbia to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Columbia to Chicago.

  • Can I find deals for business class flights from Columbia to Chicago?

    Yes. Cheapflights offers flight deals from Columbia to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Columbia, Missouri to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Columbia, Missouri to Chicago (average of $99). Flying from Columbia, Missouri to Chicago in July is currently the most expensive (average of $238). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 2 airlines flying from Columbia to Chicago

Discover the top 2 airlines that operate flights from Columbia to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$300FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$281FlexibilityNo cancel feeOn-time71%

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