$49 Cheap flight deals from Chicago (CHI) to Sikeston (STL)

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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, Feb 8 - Wed, Feb 11
ORD
O'Hare Intl.
CGI
Cape Girardeau Municipal
$142 Roundtrip, found 5 days ago
$142
Roundtrip
found 5 days ago
Select Contour Airlines flight, departing Sun, Feb 8 from O'Hare Intl. to Cape Girardeau Municipal, returning Wed, Feb 11, priced at $142 found 5 days ago
Sat, Feb 7 - Mon, Feb 9
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$272 Roundtrip, found 1 day ago
$272
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Feb 7 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Feb 9, priced at $272 found 1 day ago
Fri, Feb 6 - Sun, Feb 8
MDW
Midway Intl.
STL
Lambert-St. Louis Intl.
$339 Roundtrip, found 1 day ago
$339
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 6 from Midway Intl. to Lambert-St. Louis Intl., returning Sun, Feb 8, priced at $339 found 1 day ago
Fri, Feb 6 - Sat, Feb 7
RFD
Greater Rockford
STL
Lambert-St. Louis Intl.
$423 Roundtrip, found 6 days ago
$423
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Feb 6 from Greater Rockford to Lambert-St. Louis Intl., returning Sat, Feb 7, priced at $423 found 6 days ago

Airfares from $49 One Way, $117 Round Trip from Chicago to Sikeston

Prices starting at $117 for return flights and $49 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.

Wed, Apr 29 - Tue, May 5
ORD
Chicago
STL
St. Louis
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Apr 29 from Chicago to St. Louis, returning Tue, May 5, priced at $117 found 2 days ago
Mon, May 4 - Tue, May 5
ORD
Chicago
STL
St. Louis
$134 Roundtrip, found 8 hours ago
$134
Roundtrip
found 8 hours ago
Select United flight, departing Mon, May 4 from Chicago to St. Louis, returning Tue, May 5, priced at $134 found 8 hours ago
Mon, May 4 - Tue, May 5
ORD
Chicago
STL
St. Louis
$134 Roundtrip, found 8 hours ago
$134
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Mon, May 4 from Chicago to St. Louis, returning Tue, May 5, priced at $134 found 8 hours ago
Tue, Feb 24 - Thu, Feb 26
ORD
Chicago
STL
St. Louis
$136 Roundtrip, found 2 days ago
$136
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Feb 24 from Chicago to St. Louis, returning Thu, Feb 26, priced at $136 found 2 days ago
Tue, Feb 24 - Thu, Feb 26
ORD
Chicago
STL
St. Louis
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Feb 24 from Chicago to St. Louis, returning Thu, Feb 26, priced at $137 found 2 days ago

Sikeston economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
3.5-star property

The Wildwood Hotel

9.2/10 Wonderful! (1,600 reviews)

Mar 22 - Mar 26

4 night stay

Chicago (ORD) to St. Louis (STL)

United • Roundtrip • Coach
Price was $770, price is now $519 per person
$519
per person
found 1 day 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

The Cheshire
4.0-star property

The Cheshire

8.6/10 Excellent! (1,002 reviews)

Mar 22 - Mar 26

4 night stay

Chicago (ORD) to St. Louis (STL)

United • Roundtrip • Coach
Price was $797, price is now $635 per person
$635
per person
found 1 day ago
We always stay here when in St. Louis. Love the place. Nice atmosphere, great pub.

Reviewed on Sep 2, 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! (1,022 reviews)

Mar 22 - Mar 26

4 night stay

Chicago (ORD) to St. Louis (STL)

United • Roundtrip • Coach
Price was $789, price is now $642 per person
$642
per person
found 1 day 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

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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

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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.

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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.