$50 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, Nov 9 - Thu, Nov 13
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Nov 9 from O'Hare Intl. to Lambert-St. Louis Intl., returning Thu, Nov 13, priced at $155 found 1 day ago
Fri, Nov 7 - Sun, Nov 9
MDW
Midway Intl.
STL
Lambert-St. Louis Intl.
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Midway Intl. to Lambert-St. Louis Intl., returning Sun, Nov 9, priced at $209 found 1 day ago
Fri, Nov 7 - Wed, Nov 12
RFD
Greater Rockford
STL
Lambert-St. Louis Intl.
$534 Roundtrip, found 2 days ago
$534
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 7 from Greater Rockford to Lambert-St. Louis Intl., returning Wed, Nov 12, priced at $534 found 2 days ago

Airfares from $50 One Way, $99 Round Trip from Chicago to Sikeston

Prices starting at $99 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.

Wed, Dec 24 - Tue, Dec 30
ORD
Chicago
STL
St. Louis
$99 Roundtrip, found 2 days ago
$99
Roundtrip
found 2 days ago
Select United flight, departing Wed, Dec 24 from Chicago to St. Louis, returning Tue, Dec 30, priced at $99 found 2 days ago
Thu, Nov 13 - Sat, Nov 15
MDW
Chicago
STL
St. Louis
$122 Roundtrip, found 2 days ago
$122
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Chicago to St. Louis, returning Sat, Nov 15, priced at $122 found 2 days ago
Mon, Nov 24 - Thu, Nov 27
MDW
Chicago
STL
St. Louis
$123 Roundtrip, found 2 days ago
$123
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Nov 24 from Chicago to St. Louis, returning Thu, Nov 27, priced at $123 found 2 days ago
Thu, Dec 11 - Sat, Dec 13
ORD
Chicago
STL
St. Louis
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Dec 11 from Chicago to St. Louis, returning Sat, Dec 13, priced at $137 found 2 days ago
Thu, Dec 4 - Fri, Dec 5
ORD
Chicago
CGI
Cape Girardeau
$139 Roundtrip, found 18 hours ago
$139
Roundtrip
found 18 hours ago
Select Contour Airlines flight, departing Thu, Dec 4 from Chicago to Cape Girardeau, returning Fri, Dec 5, priced at $139 found 18 hours 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! (1,591 reviews)

Dec 13 - Dec 16

3 night stay

Chicago (ORD) to St. Louis (STL)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $520, price is now $318 per person
$318
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

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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.