$69 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.

Fri, Jun 5 - Sun, Jun 7
ORD
O'Hare Intl.
PAH
Barkley Regional
$301 Roundtrip, found 4 days ago
$301
Roundtrip
found 4 days ago
Select United flight, departing Fri, Jun 5 from O'Hare Intl. to Barkley Regional, returning Sun, Jun 7, priced at $301 found 4 days ago
Sun, Jun 7 - Wed, Jun 10
MDW
Midway Intl.
STL
Lambert-St. Louis Intl.
$349 Roundtrip, found 5 days ago
$349
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Jun 7 from Midway Intl. to Lambert-St. Louis Intl., returning Wed, Jun 10, priced at $349 found 5 days ago
Fri, Jun 5 - Sun, Jun 7
ORD
O'Hare Intl.
CGI
Cape Girardeau Municipal
$355 Roundtrip, found 2 days ago
$355
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Fri, Jun 5 from O'Hare Intl. to Cape Girardeau Municipal, returning Sun, Jun 7, priced at $355 found 2 days ago
Sun, Jun 7 - Tue, Jun 9
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$378 Roundtrip, found 16 hours ago
$378
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sun, Jun 7 from O'Hare Intl. to Lambert-St. Louis Intl., returning Tue, Jun 9, priced at $378 found 16 hours ago

Airfares from $69 One Way, $166 Round Trip from Chicago to Sikeston

Prices starting at $166 for return flights and $69 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, Aug 10 - Wed, Aug 12
ORD
Chicago
STL
St. Louis
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 10 from Chicago to St. Louis, returning Wed, Aug 12, priced at $166 found 1 day ago
Mon, Aug 10 - Wed, Aug 12
ORD
Chicago
STL
St. Louis
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select United flight, departing Mon, Aug 10 from Chicago to St. Louis, returning Wed, Aug 12, priced at $166 found 1 day ago
Mon, Aug 10 - Wed, Aug 12
ORD
Chicago
STL
St. Louis
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 10 from Chicago to St. Louis, returning Wed, Aug 12, priced at $176 found 1 day ago
Thu, Aug 27 - Wed, Sep 2
ORD
Chicago
CGI
Cape Girardeau
$178 Roundtrip, found 4 days ago
$178
Roundtrip
found 4 days ago
Select Contour Airlines flight, departing Thu, Aug 27 from Chicago to Cape Girardeau, returning Wed, Sep 2, priced at $178 found 4 days ago
Thu, Sep 24 - Sat, Sep 26
RFD
Rockford
STL
St. Louis
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Sep 24 from Rockford to St. Louis, returning Sat, Sep 26, priced at $189 found 3 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! (1,650 reviews)

Jul 11 - Jul 13

2 night stay

Chicago (ORD) to St. Louis (STL)

Frontier Airlines • Non-stop • Coach

St. Louis (STL) to Chicago (ORD)

Delta • Non-stop • Coach
Price was $638, price is now $446 per person
$446
per person
found 1 day ago
Hotel was clean but honestly, outdated. Staff was great. The continental breakfast was fine. Biggest issue was the shower. There was next to no water pressure no matter the time of day. The mattress also felt cheap. I’m not a picky person and overall, I would stay again. Just maybe not in an upgraded room. I don’t feel like it was worth it.

Reviewed on Feb 24, 2026

The Knight Center at Washington University
2.5-star property

The Knight Center at Washington University

9.4/10 Exceptional! (559 reviews)

Jul 11 - Jul 13

2 night stay

Chicago (ORD) to St. Louis (STL)

Frontier Airlines • Non-stop • Coach

St. Louis (STL) to Chicago (ORD)

Delta • Non-stop • Coach
Price was $528, price is now $454 per person
$454
per person
found 1 day ago
Very nice lobby restaurant and bar

Reviewed on Sep 15, 2025

Ameristar Casino Resort and Spa
4.5-star property

Ameristar Casino Resort and Spa

8.6/10 Excellent! (1,000 reviews)

Jul 11 - Jul 13

2 night stay

Chicago (ORD) to St. Louis (STL)

Frontier Airlines • Non-stop • Coach

St. Louis (STL) to Chicago (ORD)

Delta • Non-stop • Coach
Price was $611, price is now $532 per person
$532
per person
found 1 day ago
Room was nice. Enjoyed the pool view and spaciousness. Staff was friendly upon arrival and departure.

Reviewed on Dec 2, 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.

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.