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$163+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
COU — CHI
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
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 May 12, 2026.

This American Airlines deal was found by Cheapflights users on 5/11. 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 6/126:47 pm
COU
-
ORD
Nonstop1h 47m
American Airlines
Mon 6/154:44 pm
ORD
-
COU
Nonstop1h 33m
American Airlines
Deal found 5/11$239
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Tue 6/26:20 am
COU
-
ORD
Nonstop1h 40m
American Airlines
Sat 6/65:29 pm
ORD
-
COU
1 stop5h 17m
American Airlines
Deal found 5/11$249
This American Airlines deal was found by Cheapflights users on 5/7. 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 5/226:32 pm
COU
-
ORD
Nonstop1h 50m
American Airlines
Sat 6/67:50 pm
ORD
-
COU
Nonstop1h 34m
American Airlines
Deal found 5/7$254
This American Airlines deal was found by Cheapflights users on 5/7. 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 6/35:19 pm
COU
-
ORD
1 stop7h 23m
American Airlines
Wed 6/105:34 pm
ORD
-
COU
1 stop5h 12m
American Airlines
Deal found 5/7$268
This United Airlines deal was found by Cheapflights users on 5/7. 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 5/228:00 am
COU
-
ORD
Nonstop1h 40m
United Airlines
Tue 5/268:45 am
ORD
-
COU
Nonstop1h 33m
United Airlines
Deal found 5/7$269
This American Airlines deal was found by Cheapflights users on 5/7. 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 6/255:19 pm
COU
-
ORD
1 stop7h 20m
American Airlines
Sun 6/285:59 am
ORD
-
COU
1 stop5h 15m
American Airlines
Deal found 5/7$273
This United Airlines deal was found by Cheapflights users on 5/8. 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 9/48:00 am
COU
-
ORD
Nonstop1h 39m
United Airlines
Sun 9/67:59 am
ORD
-
COU
Nonstop1h 36m
United Airlines
Deal found 5/8$274
This American Airlines deal was found by Cheapflights users on 5/8. 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 5/226:00 am
COU
-
ORD
Nonstop1h 40m
American Airlines
Mon 5/258:20 am
ORD
-
COU
Nonstop1h 40m
American Airlines
Deal found 5/8$275

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 May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(American Airlines)

One-way from

$163
(American Airlines)

Popular in

July

Cheapest in

January

Average price

$238

Good round-trip deal

$404 or less

Good one-way deal

$263 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. 24% potential increase in price ($87 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 12, 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

Fri 10/23

5:00 am-6:41 am

Nonstop1h 41m

Chicago O'Hare Intl

Sun 10/25

11:00 pm-12:33 am

Nonstop1h 33m

$239

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Tue 6/16

6:47 pm-8:34 pm

Nonstop1h 47m

Chicago O'Hare Intl

Sun 6/21

7:50 pm-9:24 pm

Nonstop1h 34m

$239

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Wed 6/3

10:48 am-12:29 pm

Nonstop1h 41m

Chicago O'Hare Intl

Wed 6/10

8:40 am-10:13 am

Nonstop1h 33m

$239
Quickest round-trip

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Sat 6/13

8:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Wed 6/17

10:00 pm-11:33 pm

Nonstop1h 33m

$239

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Thu 7/9

10:49 am-12:30 pm

Nonstop1h 41m

Chicago O'Hare Intl

Sun 7/12

8:40 am-10:13 am

Nonstop1h 33m

$239

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Tue 8/4

8:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Mon 8/10

10:00 pm-11:33 pm

Nonstop1h 33m

$239

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Thu 6/25

6:00 am-7:38 am

Nonstop1h 38m

Chicago O'Hare Intl

Sun 6/28

5:59 am-11:14 am

1 stop5h 15m

$248

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Thu 6/4

7:39 pm-12:44 am

1 stop5h 05m

Chicago O'Hare Intl

Sun 6/7

8:30 am-10:06 am

Nonstop1h 36m

$248

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Fri 7/24

6:32 pm-8:23 pm

Nonstop1h 51m

Chicago O'Hare Intl

Mon 7/27

4:29 pm-6:01 pm

Nonstop1h 32m

$254

ColumbiaChicago

COU - ORD

COUORD

Columbia Regional

Wed 6/3

5:19 pm-12:42 am

1 stop7h 23m

Chicago O'Hare Intl

Sat 6/6

4:49 pm-10:46 pm

1 stop5h 57m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 22 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 May.
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 May 12, 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 evening, which can drop the price by up to 15% versus a flight at noon.

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 May 9, 2026.

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

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 May 12, 2026.

The most flights from COU to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 on average).

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

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 May 12, 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
9,701 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,701 reviews
United Airlines
7.4
Good
9,701 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,661 reviews
United Airlines
7.4
Good
9,701 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 $239, United Airlines can have you in Chicago from Columbia, Missouri in 1h 41m. 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 33% 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: Qatar Airways (87%), American Airlines (75%), Envoy Air (75%).

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

    The cheapest flight price from Columbia, Missouri to Chicago is $183. On average you can expect to pay $461. 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 May 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$294FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$289FlexibilityNo cancel feeOn-time71%

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