$59 Cheap flight deals from Chicago (CHI) to Boonville (JEF)

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 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.

Fri, Apr 10 - Sun, Apr 12
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$253 Roundtrip, just found
$253
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 $253 just found
Fri, Apr 10 - Sun, Apr 12
RFD
Greater Rockford
COU
Columbia Regional
$352 Roundtrip, found 4 days ago
$352
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Apr 10 from Greater Rockford to Columbia Regional, returning Sun, Apr 12, priced at $352 found 4 days ago
Fri, Apr 10 - Sun, Apr 12
ORD
O'Hare Intl.
COU
Columbia Regional
$468 Roundtrip, found 23 hours ago
$468
Roundtrip
found 23 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 23 hours ago
Sat, Apr 11 - Sun, Apr 12
MDW
Midway Intl.
STL
Lambert-St. Louis Intl.
$511 Roundtrip, found 4 days ago
$511
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Apr 11 from Midway Intl. to Lambert-St. Louis Intl., returning Sun, Apr 12, priced at $511 found 4 days ago

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

Prices starting at $119 for return flights and $59 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.

Tue, May 19 - Tue, May 26
ORD
Chicago
STL
St. Louis
$119 Roundtrip, found 3 days ago
$119
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, May 19 from Chicago to St. Louis, returning Tue, May 26, priced at $119 found 3 days ago
Tue, May 19 - Tue, May 26
ORD
Chicago
STL
St. Louis
$119 Roundtrip, found 3 days ago
$119
Roundtrip
found 3 days ago
Select United flight, departing Tue, May 19 from Chicago to St. Louis, returning Tue, May 26, priced at $119 found 3 days ago
Tue, May 19 - Tue, May 26
ORD
Chicago
STL
St. Louis
$139 Roundtrip, found 3 days ago
$139
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, May 19 from Chicago to St. Louis, returning Tue, May 26, priced at $139 found 3 days ago
Mon, Apr 27 - Thu, Apr 30
MDW
Chicago
STL
St. Louis
$181 Roundtrip, found 4 days ago
$181
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Chicago to St. Louis, returning Thu, Apr 30, priced at $181 found 4 days ago
Wed, May 6 - Mon, May 11
ORD
Chicago
MCI
Kansas City
$183 Roundtrip, just found
$183
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 6 from Chicago to Kansas City, returning Mon, May 11, priced at $183 just found

Boonville economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Clayton/St. Louis-Galleria Area
3.0-star property

Hampton Inn & Suites Clayton/St. Louis-Galleria Area

9/10 Wonderful! (944 reviews)

May 9 - May 12

3 night stay

Chicago (CHI) to St. Louis (STL)

United • Roundtrip • Coach
Price was $434, price is now $333 per person
$333
per person
found 1 day ago
Black bananas at breakfast two days in a row over easter weekend. Bad coffee in the room, but downstairs coffee was excellent. Maid service non-existent even when we called for it. No pick-up of used bath towels, having to call every evening for pickup of wet towels and asking for new ones ... even when the hotel was not busy. I do love the location and staff members nice, but not taking care of requests for service.

Reviewed on Apr 20, 2022

Best Western Plus KC Speedway Inn & Suites
3.0-star property

Best Western Plus KC Speedway Inn & Suites

6.8/10 (1,003 reviews)

May 8 - May 10

2 night stay

Chicago (CHI) to Kansas City (MCI)

Southwest Airlines • Coach

Kansas City (MCI) to Chicago (CHI)

Frontier Airlines • Coach
Price was $622, price is now $420 per person
$420
per person
found 1 day ago
Darrell, The front counter clerk was by far the best host I have ever had. He was so nice and helpful, went over and above to help me and my family. I hope the Hotel appreciates what a great employee they have in him.

Reviewed on Jul 4, 2023

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! (1,065 reviews)

May 9 - May 12

3 night stay

Chicago (CHI) to St. Louis (STL)

United • Roundtrip • Coach
Price was $463, price is now $340 per person
$340
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

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

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

Orbitz is your one-stop source for great online deals on {origin.name} to Boonville flights. With our cutting-edge mobile tools and low fares, you are never far from finding fantastic savings on flights from Chicago to Boonville.

Unbeatable Deals for Flights From Chicago to Boonville

If you are looking for the cheapest {origin.name} to Boonville flights, you can save your money and your sanity by booking your air fare through Orbitz. Our low price guarantee for international and domestic flights leaves more money in your wallet to spend on activities, restaurants, attractions, and other adventures in your destination.

Book Cheap Chicago to Boonville Flights Anytime

There is no need to hover by your computer for the latest air ticket deals—our free mobile apps keep you informed. Find discount air fare and accommodations, research your destination, and buy bargain flights from Chicago to Boonville on your Android device, iPad, or iPhone. Stay updated about any updates, disruptions, and delays to your flight by signing up for instant email or text alerts

Don't Miss Out on Frequent Flyer Points

You can still earn points or miles for your frequent flyer program when you take advantage of our low fare Chicago to Boonville flights. When you book through Orbitz, you just need to provide your frequent flyer details to get credit for qualifying flights.

Easy Flight Cancellation

In most cases, you can cancel flights from Chicago to Boonville online with the same ease as you booked them.

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.