$74 Cheap flight deals from Chicago (CHI) to Boonville (JEF)

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This Weekend's Flight Deals from Chicago to Boonville

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, Apr 5 - Sun, Apr 12
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$281 Roundtrip, found 3 days ago
$281
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Apr 5 from O'Hare Intl. to Lambert-St. Louis Intl., returning Sun, Apr 12, priced at $281 found 3 days ago
Sat, Apr 4 - Sun, Apr 5
ORD
O'Hare Intl.
COU
Columbia Regional
$399 Roundtrip, found 17 hours ago
$399
Roundtrip
found 17 hours ago
Select United flight, departing Sat, Apr 4 from O'Hare Intl. to Columbia Regional, returning Sun, Apr 5, priced at $399 found 17 hours ago
Fri, Apr 3 - Mon, Apr 6
MDW
Midway Intl.
MCI
Kansas City Intl.
$517 Roundtrip, found 17 hours ago
$517
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Apr 3 from Midway Intl. to Kansas City Intl., returning Mon, Apr 6, priced at $517 found 17 hours ago
Fri, Apr 3 - Mon, Apr 6
ORD
O'Hare Intl.
MCI
Kansas City Intl.
$517 Roundtrip, found 17 hours ago
$517
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Apr 3 from O'Hare Intl. to Kansas City Intl., returning Mon, Apr 6, priced at $517 found 17 hours ago

Airfares from $74 One Way, $163 Round Trip from Chicago to Boonville

Prices starting at $163 for return flights and $74 for one-way flights to Boonville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 9 - Sun, May 10
ORD
Chicago
STL
St. Louis
$163 Roundtrip, found 3 days ago
$163
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 9 from Chicago to St. Louis, returning Sun, May 10, priced at $163 found 3 days ago
Wed, Apr 15 - Wed, May 6
ORD
Chicago
MCI
Kansas City
$175 Roundtrip, found 4 days ago
$175
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Apr 15 from Chicago to Kansas City, returning Wed, May 6, priced at $175 found 4 days ago
Wed, Apr 22 - Sat, Apr 25
MDW
Chicago
STL
St. Louis
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Apr 22 from Chicago to St. Louis, returning Sat, Apr 25, priced at $199 found 1 day ago
Sat, May 2 - Tue, May 5
ORD
Chicago
STL
St. Louis
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, May 2 from Chicago to St. Louis, returning Tue, May 5, priced at $199 found 1 day ago
Sat, May 2 - Tue, May 5
ORD
Chicago
STL
St. Louis
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 2 from Chicago to St. Louis, returning Tue, May 5, priced at $199 found 1 day ago

Boonville 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! (1,620 reviews)

May 1 - May 3

2 night stay

Chicago (CHI) to St. Louis (STL)

Southwest Airlines • Coach

St. Louis (STL) to Chicago (CHI)

American Airlines • Coach
Price was $716, price is now $510 per person
$510
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

Ameristar Casino Resort and Spa
4.5-star property

Ameristar Casino Resort and Spa

8.4/10 Very Good! (1,000 reviews)

May 1 - May 3

2 night stay

Chicago (CHI) to St. Louis (STL)

Southwest Airlines • Coach

St. Louis (STL) to Chicago (CHI)

American Airlines • Coach
Price was $685, price is now $561 per person
$561
per person
found 16 hours ago
Room was nice. Enjoyed the pool view and spaciousness. Staff was friendly upon arrival and departure.

Reviewed on Dec 2, 2025

21C Museum Hotel St Louis
4.5-star property

21C Museum Hotel St Louis

9/10 Wonderful! (1,647 reviews)

May 1 - May 3

2 night stay

Chicago (CHI) to St. Louis (STL)

Southwest Airlines • Coach

St. Louis (STL) to Chicago (CHI)

American Airlines • Coach
Price was $645, price is now $555 per person
$555
per person
found 24 hours ago
The cafe that sold breakfast ran out of healthy options each morning (yogurt parfait cup/ overnight oats & quinoa $8 each) They had other plates, egg with meat, etc that looked nice fwiw. Cute gift shop in the cafe. Fashionable hotel with no real 'front desk' just a checkin counter, but volunteers were staffing a St. Louis info table in the lobby while we were there- very friendly. The bar/tapas restaurant across the lobby was fun, $$, and kitchen closed at 10 or so when our events got out so I didn't get to try it. LOVED the historic building, originally a YMCA, the handsome billiards room and the terrific tiled pool with vaulted ceiling- they don't make them like that anymore. Steam room, sauna, showers were great- bring a room towel in case the spa runs short! Open til 10:30p or 11p fyi. Art Museum on the 2nd floor is free to visitors, and had some challenging, gorgeous, funny, and thought-provoking art. Historic Campbell Mansion next door was a neat contrast and a quick peek into the high Victorian era. Glad I went, would stay again

Reviewed on Jan 14, 2026

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More About Flying To Boonville from Chicago

Route Information for Flights from Chicago to Boonville

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

Chicago to Boonville

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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.