$50 Cheap flight deals from Chicago (CHI) to Sikeston (STL)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Sikeston

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, Mar 22 - Mon, Mar 23
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$501 Roundtrip, found 1 day ago
$501
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Mar 22 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Mar 23, priced at $501 found 1 day ago
Fri, Mar 20 - Sun, Mar 22
RFD
Greater Rockford
STL
Lambert-St. Louis Intl.
$648 Roundtrip, found 4 days ago
$648
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Mar 20 from Greater Rockford to Lambert-St. Louis Intl., returning Sun, Mar 22, priced at $648 found 4 days ago
Fri, Mar 20 - Sun, Mar 22
MDW
Midway Intl.
STL
Lambert-St. Louis Intl.
$783 Roundtrip, found 2 hours ago
$783
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Fri, Mar 20 from Midway Intl. to Lambert-St. Louis Intl., returning Sun, Mar 22, priced at $783 found 2 hours ago

Airfares from $50 One Way, $139 Round Trip from Chicago to Sikeston

Prices starting at $139 for return flights and $50 for one-way flights to Sikeston 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, Mar 30 - Thu, Apr 2
ORD
Chicago
CGI
Cape Girardeau
$139 Roundtrip, found 2 hours ago
$139
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Mon, Mar 30 from Chicago to Cape Girardeau, returning Thu, Apr 2, priced at $139 found 2 hours ago
Wed, Apr 8 - Sun, Apr 12
ORD
Chicago
CGI
Cape Girardeau
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
Select Contour Airlines flight, departing Wed, Apr 8 from Chicago to Cape Girardeau, returning Sun, Apr 12, priced at $142 found 4 days ago
Fri, Mar 27 - Tue, Mar 31
ORD
Chicago
CGI
Cape Girardeau
$144 Roundtrip, found 4 days ago
$144
Roundtrip
found 4 days ago
Select Contour Airlines flight, departing Fri, Mar 27 from Chicago to Cape Girardeau, returning Tue, Mar 31, priced at $144 found 4 days ago
Mon, Apr 6 - Tue, Apr 7
ORD
Chicago
STL
St. Louis
$156 Roundtrip, found 6 days ago
$156
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Apr 6 from Chicago to St. Louis, returning Tue, Apr 7, priced at $156 found 6 days ago
Mon, Apr 6 - Tue, Apr 7
ORD
Chicago
STL
St. Louis
$158 Roundtrip, found 6 days ago
$158
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Apr 6 from Chicago to St. Louis, returning Tue, Apr 7, priced at $158 found 6 days ago

Sikeston economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Knight Center at Washington University
2.5-star property

The Knight Center at Washington University

9.4/10 Exceptional! (496 reviews)

Apr 24 - Apr 26

2 night stay

Chicago (ORD) to St. Louis (STL)

American Airlines • Roundtrip • Coach
Price was $606, price is now $534 per person
$534
per person
found 4 hours ago
Very nice lobby restaurant and bar

Reviewed on Sep 15, 2025

The Wildwood Hotel
3.5-star property

The Wildwood Hotel

9.2/10 Wonderful! (1,620 reviews)

Apr 24 - Apr 26

2 night stay

Chicago (ORD) to St. Louis (STL)

American Airlines • Roundtrip • Coach
Price was $840, price is now $579 per person
$579
per person
found 4 hours ago
This hotel was fantastic! Check in was easy with friendly staff, the room was beautiful and well appointed. Breakfast was advertised as a Continental, however they had hot options as well, which was great. Every staff member we saw in the hotel said hi and was friendly. I would definitely stay here again!

Reviewed on Oct 16, 2025

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
4.0-star property

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

8.8/10 Excellent! (1,060 reviews)

Apr 24 - Apr 26

2 night stay

Chicago (ORD) to St. Louis (STL)

American Airlines • Roundtrip • Coach
Price was $738, price is now $641 per person
$641
per person
found 4 hours ago
Perfect location for stay after event at Powell Theater. Roof top bar was nice although a little pricey. Room was unique, clean, and comfortable. Parking is additional.

Reviewed on Jan 18, 2026

Don't see what you're looking for?
See all available trips from Chicago to Sikeston
View all trips

More About Flying To Sikeston from Chicago

Route Information for Flights from Chicago to Sikeston

Origin Airport IATA Code
CHI
Destination Airport IATA Code
STL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Sikeston

Using Orbitz can save you a significant amount of money and time when booking Chicago to Sikeston flights. With cutting-edge mobile tools for on-the-move travel planning and guaranteed low prices, Orbitz is the ultimate resource for travelers looking for great deals.

Book Your Chicago to Sikeston Flights From Any Location

Orbitz now offers free apps for iPad, iPhone, and Android users. You can use Orbitz on these devices to search for affordable fares and to book flights from Chicago to Sikeston. Mobile apps also allow users to view, compare, and book hotel rooms with just a few taps on the screen and let you access up-to-date flight and baggage claim information in a matter of seconds.

Fly Cheap and Boost Your Frequent Flyer Miles

Earn miles or points on select Chicago to Sikeston flights to boost your frequent flyer travel rewards. When using Orbitz to book domestic or international flights, include your frequent flyer numbers or add these details to your Orbitz user profile so they are included with your reservation.

Keep Everyone Updated With Flight Alerts

Orbitz is the ideal way to book flights from Chicago to Sikeston. Free Orbitz alerts can be sent to you and as many as six of your contacts about changes to your Chicago to Sikeston flights. This keeps everyone notified of flight delays or any other disruptions that might impact your arrival time.

Orbitz Makes It Easy to Plan Your Trips on a Budget

You can always find affordable flights from Chicago to Sikeston on Orbitz. Use different airlines to book arrival and departure flights, take advantage of vacation package deals, and secure exclusive rewards.

Frequently asked questions

Are there non-stop flights from Chicago to Sikeston?
There is. You can fly straight from Chicago to Sikeston with United Airlines. It's the only airline with nonstop services from ORD to Cape Girardeau Municipal Airport (CGI).
What is the shortest flight from Chicago to Sikeston?
The journey from Chicago to Sikeston can be as fast as 1 hour and 57 minutes. With a leisurely flight time like this, why not take off on a spur-of-the-moment getaway?
What airlines fly from Chicago to Sikeston most frequently?
Lock in your Chicago to Sikeston journey with a United Airlines flight. With 52 per month, this airline operates the most flights between these two destinations.
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.

More Destinations

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.