$39 Cheap flight deals from Columbia (JEF) to Chicago (CHI)

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This Weekend's Flight Deals from Columbia to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, May 4 - Thu, May 15
STL
Lambert-St. Louis Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 23 hours ago
$181
Roundtrip
found 23 hours ago
Select Southern Airways Express flight, departing Sun, May 4 from Lambert-St. Louis Intl. to O'Hare Intl., returning Thu, May 15, priced at $181 found 23 hours ago
Sun, May 4 - Sun, May 11
STL
Lambert-St. Louis Intl.
MDW
Midway Intl.
$202 Roundtrip, found 23 hours ago
$202
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sun, May 4 from Lambert-St. Louis Intl. to Midway Intl., returning Sun, May 11, priced at $202 found 23 hours ago
Sun, May 4 - Thu, May 8
MCI
Kansas City Intl.
MDW
Midway Intl.
$230 Roundtrip, found 15 hours ago
$230
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sun, May 4 from Kansas City Intl. to Midway Intl., returning Thu, May 8, priced at $230 found 15 hours ago
Sat, May 3 - Wed, May 21
COU
Columbia Regional
ORD
O'Hare Intl.
$385 Roundtrip, found 3 days ago
$385
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, May 3 from Columbia Regional to O'Hare Intl., returning Wed, May 21, priced at $385 found 3 days ago

Airfares from $39 One Way, $77 Round Trip from Columbia to Chicago

Prices starting at $77 for return flights and $39 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Jun 30 - Wed, Jul 2
MCI
Kansas City
ORD
Chicago
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jun 30 from Kansas City to Chicago, returning Wed, Jul 2, priced at $77 found 1 day ago
Mon, Jun 2 - Thu, Jun 5
STL
St. Louis
ORD
Chicago
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jun 2 from St. Louis to Chicago, returning Thu, Jun 5, priced at $77 found 1 day ago
Mon, Jul 7 - Mon, Aug 4
STL
St. Louis
ORD
Chicago
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jul 7 from St. Louis to Chicago, returning Mon, Aug 4, priced at $80 found 1 day ago
Thu, Jun 5 - Mon, Jun 9
MCI
Kansas City
MDW
Chicago
$87 Roundtrip, found 11 hours ago
$87
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Thu, Jun 5 from Kansas City to Chicago, returning Mon, Jun 9, priced at $87 found 11 hours ago
Thu, Jul 17 - Tue, Jul 29
MCI
Kansas City
ORD
Chicago
$91 Roundtrip, found 1 day ago
$91
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jul 17 from Kansas City to Chicago, returning Tue, Jul 29, priced at $91 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Chicago Downtown, Autograph Collection by Marriott
4.0-star property

Hotel Chicago Downtown, Autograph Collection by Marriott

9/10 Wonderful! (1,001 reviews)

Jun 19 - Jun 22

3 night stay

Kansas City (MCI) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
It’s a very nice hotel

Reviewed on Mar 21, 2025

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (295 reviews)

Jun 5 - Jun 8

3 night stay

Kansas City (MCI) to Chicago (ORD)

United • Coach

Chicago (ORD) to Kansas City (MCI)

Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates

Reviewed on Feb 16, 2024

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More About Flying To Chicago from Columbia

Route Information for Flights from Columbia to Chicago

Origin Airport IATA Code
JEF
Destination Airport IATA Code
CHI
Distance
258 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Austrian, Aer Lingus, Emirates, Copa Airlines, Air New Zealand, United Airlines, Alaska Airlines, Cathay Pacific, Avianca, Turkish Airlines, Royal Jordanian, Finnair, Iberia, ANA, Lufthansa, British Airways, Gulf Air
Earliest Flight Arrival
12:05PM UTC
Latest Flight Arrival
12:19AM UTC

Columbia to Chicago

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Frequently asked questions

Are there non-stop flights from Columbia to Chicago?
Yes, you’ll be pleased to hear that you can fly straight from STL to Chicago, IL (ORD-O’Hare Intl.). Direct flights are offered by United Airlines and American Airlines.
What is the shortest flight from Columbia to Chicago?
If conditions are good and all goes according to plan, you could be stepping off the plane at Chicago, IL (ORD-O’Hare Intl.) from Lambert-St. Louis Intl. Airport (STL) in as little as 1 hour. With such a short flight time, consider traveling with just hand luggage.
What airlines fly from Columbia to Chicago most frequently?
United Airlines (UA) operates 212 flights every month between St. Louis, MO (STL-Lambert-St. Louis Intl.) to Chicago, IL (ORD-O’Hare Intl.). Your next great adventure is only a few clicks away. Alternatively, secure a seat with American Airlines (AA). You’ll have 165 monthly flights between Columbia and Chicago to choose from with this airline.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.