$59 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.

Sat, Oct 10 - Mon, Oct 12
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$409 Roundtrip, just found
$409
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 10 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Oct 12, priced at $409 just found
Fri, Oct 9 - Sun, Oct 11
MDW
Midway Intl.
STL
Lambert-St. Louis Intl.
$501 Roundtrip, found 15 hours ago
$501
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Fri, Oct 9 from Midway Intl. to Lambert-St. Louis Intl., returning Sun, Oct 11, priced at $501 found 15 hours ago

Airfares from $59 One Way, $137 Round Trip from Chicago to Sikeston

Prices starting at $137 for return flights and $59 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, Oct 28 - Fri, Oct 30
MDW
Chicago
STL
St. Louis
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Oct 28 from Chicago to St. Louis, returning Fri, Oct 30, priced at $137 found 6 days ago
Wed, Oct 28 - Fri, Oct 30
ORD
Chicago
STL
St. Louis
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Oct 28 from Chicago to St. Louis, returning Fri, Oct 30, priced at $137 found 6 days ago
Fri, Nov 6 - Mon, Nov 9
MDW
Chicago
STL
St. Louis
$195 Roundtrip, found 4 days ago
$195
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Nov 6 from Chicago to St. Louis, returning Mon, Nov 9, priced at $195 found 4 days ago
Thu, Oct 22 - Wed, Oct 28
ORD
Chicago
CGI
Cape Girardeau
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Thu, Oct 22 from Chicago to Cape Girardeau, returning Wed, Oct 28, priced at $198 found 3 days ago
Wed, Nov 4 - Thu, Nov 5
MDW
Chicago
STL
St. Louis
$245 Roundtrip, found 3 hours ago
$245
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Chicago to St. Louis, returning Thu, Nov 5, priced at $245 found 3 hours ago

Sikeston economy flight packages

Price found within the past 48 hours. Click for updated prices.
The West End
2.0-star property

The West End

8.6/10 Excellent! (650 reviews)

Nov 20 - Nov 22

2 night stay

Chicago (ORD) to St. Louis (STL)

American Airlines • Roundtrip • Coach
Price was $448, price is now $400 per person
$400
per person
found 23 hours ago
Great service, front desk very helpful and since I had a procedure at BJU there was free parking in there garage. No breakfast though. And would love to have had a recliner in the room but will be back.

Reviewed on Oct 3, 2026

The Wildwood Hotel
3.5-star property

The Wildwood Hotel

9.2/10 Wonderful! (1,679 reviews)

Nov 20 - Nov 22

2 night stay

Chicago (ORD) to St. Louis (STL)

American Airlines • Roundtrip • Coach
Price was $704, price is now $461 per person
$461
per person
found 23 hours ago
Room was clean, yet picures and description are a bit deceiving. Overall, stay was good and would come back again.

Reviewed on Oct 4, 2026

Hyatt Regency St. Louis at The Arch
4.0-star property

Hyatt Regency St. Louis at The Arch

8.6/10 Excellent! (4,290 reviews)

Nov 20 - Nov 22

2 night stay

Chicago (ORD) to St. Louis (STL)

American Airlines • Roundtrip • Coach
Price was $554, price is now $509 per person
$509
per person
found 23 hours ago

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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

If you feel you cannot afford the costs involved to your dream trip to a local or international destination happen, think again! Orbitz gives you incredible deals on flights from Chicago to Sikeston. Now you can book guaranteed low fares for Chicago to Sikeston flights and plan your trip with confidence.

Great deals on flights from Chicago to Sikeston

Cheap airfares on Chicago to Sikeston flights allow you to stick to your budget and still have a great trip. We give you guaranteed low prices and make it easy to research and book discount flights using our website. Additionally, you can add your frequent flyer numbers to your Orbitz account profile, and this information will automatically be included on all your future reservations for qualified flights from Chicago to Sikeston.

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Chicago to Sikeston flights at discounted rates

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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.