$59 Cheap flight deals from Chicago (CHI) to Macon (STL)

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This Weekend's Flight Deals from Chicago to Macon

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, Apr 10 - Sun, Apr 12
ORD
O'Hare Intl.
IRK
Kirksville Municipal
$248 Roundtrip, found 4 days ago
$248
Roundtrip
found 4 days ago
Select Contour Airlines flight, departing Fri, Apr 10 from O'Hare Intl. to Kirksville Municipal, returning Sun, Apr 12, priced at $248 found 4 days ago
Fri, Apr 10 - Sun, Apr 12
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$265 Roundtrip, just found
$265
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Apr 10 from O'Hare Intl. to Lambert-St. Louis Intl., returning Sun, Apr 12, priced at $265 just found
Fri, Apr 10 - Sun, Apr 12
RFD
Greater Rockford
COU
Columbia Regional
$352 Roundtrip, found 5 days ago
$352
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Apr 10 from Greater Rockford to Columbia Regional, returning Sun, Apr 12, priced at $352 found 5 days ago
Fri, Apr 10 - Sun, Apr 12
ORD
O'Hare Intl.
COU
Columbia Regional
$468 Roundtrip, found 18 hours ago
$468
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Fri, Apr 10 from O'Hare Intl. to Columbia Regional, returning Sun, Apr 12, priced at $468 found 18 hours ago

Airfares from $59 One Way, $119 Round Trip from Chicago to Macon

Prices starting at $119 for return flights and $59 for one-way flights to Macon were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, May 19 - Tue, May 26
ORD
Chicago
STL
St. Louis
$119 Roundtrip, found 4 days ago
$119
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, May 19 from Chicago to St. Louis, returning Tue, May 26, priced at $119 found 4 days ago
Tue, May 19 - Tue, May 26
ORD
Chicago
STL
St. Louis
$119 Roundtrip, found 4 days ago
$119
Roundtrip
found 4 days ago
Select United flight, departing Tue, May 19 from Chicago to St. Louis, returning Tue, May 26, priced at $119 found 4 days ago
Fri, Apr 24 - Mon, Apr 27
ORD
Chicago
IRK
Kirksville
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Fri, Apr 24 from Chicago to Kirksville, returning Mon, Apr 27, priced at $139 found 2 days ago
Tue, May 19 - Tue, May 26
ORD
Chicago
STL
St. Louis
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, May 19 from Chicago to St. Louis, returning Tue, May 26, priced at $139 found 4 days ago
Thu, Apr 30 - Mon, May 4
ORD
Chicago
STL
St. Louis
$153 Roundtrip, just found
$153
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Apr 30 from Chicago to St. Louis, returning Mon, May 4, priced at $153 just found

Macon 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! (1,627 reviews)

May 8 - May 11

3 night stay

Chicago (MDW) to St. Louis (STL)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $680, price is now $427 per person
$427
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

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! (1,049 reviews)

May 8 - May 11

3 night stay

Chicago (MDW) to St. Louis (STL)

Southwest Airlines • Roundtrip • Coach
Price was $651, price is now $493 per person
$493
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

The Cheshire
4.0-star property

The Cheshire

8.6/10 Excellent! (1,011 reviews)

May 8 - May 11

3 night stay

Chicago (MDW) to St. Louis (STL)

Southwest Airlines • Roundtrip • Coach
Price was $648, price is now $496 per person
$496
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

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More About Flying To Macon from Chicago

Route Information for Flights from Chicago to Macon

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

Chicago to Macon

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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.