$59 Cheap flight deals from Chicago (CHI) to Shelbyville (CMI)

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 Shelbyville

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, Nov 14 - Tue, Nov 17
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$822 Roundtrip, found 4 days ago
$822
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Nov 14 from O'Hare Intl. to Lambert-St. Louis Intl., returning Tue, Nov 17, priced at $822 found 4 days ago

Airfares from $59 One Way, $117 Round Trip from Chicago to Shelbyville

Prices starting at $117 for return flights and $59 for one-way flights to Shelbyville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Dec 18 - Mon, Dec 21
ORD
Chicago
STL
St. Louis
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Dec 18 from Chicago to St. Louis, returning Mon, Dec 21, priced at $117 found 6 days ago
Tue, Dec 1 - Sat, Dec 5
ORD
Chicago
STL
St. Louis
$128 Roundtrip, found 19 hours ago
$128
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Tue, Dec 1 from Chicago to St. Louis, returning Sat, Dec 5, priced at $128 found 19 hours ago
Sat, Dec 5 - Mon, Dec 7
ORD
Chicago
STL
St. Louis
$149 Roundtrip, found 6 hours ago
$149
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Dec 5 from Chicago to St. Louis, returning Mon, Dec 7, priced at $149 found 6 hours ago
Thu, Dec 3 - Sat, Dec 5
ORD
Chicago
STL
St. Louis
$149 Roundtrip, found 9 hours ago
$149
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Chicago to St. Louis, returning Sat, Dec 5, priced at $149 found 9 hours ago
Sat, Dec 5 - Mon, Dec 7
ORD
Chicago
STL
St. Louis
$153 Roundtrip, found 6 hours ago
$153
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Dec 5 from Chicago to St. Louis, returning Mon, Dec 7, priced at $153 found 6 hours ago

Shelbyville economy flight packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Rolla, MO
2.0-star property

Motel 6 Rolla, MO

6.6/10 (290 reviews)

Dec 26 - Dec 30

4 night stay

Chicago (ORD) to St. Louis (STL)

United • Roundtrip • Coach
Price was $441, price is now $390 per person
$390
per person
found 1 day ago
I stayed there last night. The room was clean, the property was clean. My only issue was that I was asked to wait 15 minutes prior to entering tje room so they could make sure it was clean. I checked in late, after 10 pm so I think they should've known if the room was clean. I slept really good and the bed was comfortable. No issues with anything else.

Reviewed on Nov 6, 2026

Hermann Grain Bins BNB
2.0-star property

Hermann Grain Bins BNB

6/10 (2 reviews)

Dec 26 - Dec 30

4 night stay

Chicago (ORD) to St. Louis (STL)

United • Roundtrip • Coach
Price was $1,418, price is now $1,220 per person
$1,220
per person
found 1 day ago
Our stay at the Grain Bins was excellent! The spaces were exactly as described! Everything was very clean and well appointed. Communication was great. We especially enjoyed relaxing around the fire pit. Homemade breakfast each morning was such a nice touch! Added bonus: The Hermann trolley was able to pick us up and drop us back off at the end of the day. Highly recommend staying at the Hermann Grain Bins and hope to stay again in the future!

Reviewed on Oct 30, 2026

Best Western Coachlight
2.5-star property

Best Western Coachlight

7.6/10 Good! (682 reviews)

Dec 26 - Dec 30

4 night stay

Chicago (ORD) to St. Louis (STL)

United • Roundtrip • Coach
Price was $476, price is now $444 per person
$444
per person
found 1 day ago
Bed was hard. Freezer part of the mini fridge door was broke.

Reviewed on Nov 3, 2026

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

More About Flying To Shelbyville from Chicago

Route Information for Flights from Chicago to Shelbyville

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

Chicago to Shelbyville

The perfect trip begins with Orbitz. From booking your flights from Chicago to Shelbyville to finding the best hotels, Orbitz has got it covered.

Stress-free Searching

With an easy to use system, Orbitz takes the stress and expense out of travel. Not only does Orbitz match your Chicago to Shelbyville flights to your ideal hotel, the Display Matrix shows your deals and discounts, including free nights and other savings.

Be One Step Ahead

Need to know what is going on at the airport before you get there? With Orbitz’s free alerts service, you can quickly find out about any booking changes, or flight from Chicago to Shelbyville disruptions, saving you hours of wasted time. And if you are being picked up at the airport after your Chicago to Shelbyville flights, have alerts sent straight to your contact’s mobile phone or email.

Cutting-Edge Mobile Tools

Find the best price on flights from Chicago to Shelbyville with Orbitz’s mobile apps for iPhone and Android. Use m.orbitz.com on your mobile browser to check your gate, baggage allowance and delays, or find exclusive deals on hotels only available to mobile users.

We Work, you Rest and Play

Not only does booking with us ensure guaranteed low prices, but Orbitz does the hard work, leaving you to relax. Just tell us what you want, from Chicago to Shelbyville flights, to great deals on hotels and car rental, and activities and tours, and we will do all the rest.

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.