$59 Cheap flight deals from Chicago (CHI) to Rolla (SGF)

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This Weekend's Flight Deals from Chicago to Rolla

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, Aug 14 - Sun, Aug 16
ORD
O'Hare Intl.
COU
Columbia Regional
$343 Roundtrip, found 5 days ago
$343
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Aug 14 from O'Hare Intl. to Columbia Regional, returning Sun, Aug 16, priced at $343 found 5 days ago
Sun, Aug 16 - Mon, Aug 17
ORD
O'Hare Intl.
STL
Lambert-St. Louis Intl.
$355 Roundtrip, found 22 hours ago
$355
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sun, Aug 16 from O'Hare Intl. to Lambert-St. Louis Intl., returning Mon, Aug 17, priced at $355 found 22 hours ago
Sat, Aug 15 - Tue, Aug 18
ORD
O'Hare Intl.
SGF
Springfield-Branson National
$371 Roundtrip, found 22 hours ago
$371
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Aug 15 from O'Hare Intl. to Springfield-Branson National, returning Tue, Aug 18, priced at $371 found 22 hours ago

Airfares from $59 One Way, $132 Round Trip from Chicago to Rolla

Prices starting at $132 for return flights and $59 for one-way flights to Rolla 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, Sep 9 - Fri, Sep 11
ORD
Chicago
STL
St. Louis
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Chicago to St. Louis, returning Fri, Sep 11, priced at $132 found 6 days ago
Wed, Sep 9 - Fri, Sep 11
ORD
Chicago
STL
St. Louis
$136 Roundtrip, found 6 days ago
$136
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Sep 9 from Chicago to St. Louis, returning Fri, Sep 11, priced at $136 found 6 days ago
Wed, Sep 9 - Fri, Sep 11
ORD
Chicago
STL
St. Louis
$136 Roundtrip, found 6 days ago
$136
Roundtrip
found 6 days ago
Select United flight, departing Wed, Sep 9 from Chicago to St. Louis, returning Fri, Sep 11, priced at $136 found 6 days ago
Fri, Sep 18 - Mon, Sep 21
MDW
Chicago
STL
St. Louis
$219 Roundtrip, found 4 days ago
$219
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Sep 18 from Chicago to St. Louis, returning Mon, Sep 21, priced at $219 found 4 days ago
Thu, Sep 17 - Sun, Sep 20
RFD
Rockford
COU
Columbia
$246 Roundtrip, found 1 day ago
$246
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 17 from Rockford to Columbia, returning Sun, Sep 20, priced at $246 found 1 day ago

Rolla 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! (1,672 reviews)

Sep 17 - Sep 20

3 night stay

Chicago (CHI) to St. Louis (STL)

Southwest Airlines • Coach

St. Louis (STL) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
Price was $800, price is now $515 per person
$515
per person
found 17 hours ago
Very nice hotel in the middle of Wildwood. We are visiting relatives and it was great to find a good hotel close to them.

Reviewed on Aug 11, 2026

The Cheshire
4.0-star property

The Cheshire

8.8/10 Excellent! (1,006 reviews)

Sep 17 - Sep 20

3 night stay

Chicago (CHI) to St. Louis (STL)

Southwest Airlines • Coach

St. Louis (STL) to Chicago (CHI)

American Airlines • Coach
Price was $781, price is now $607 per person
$607
per person
found 17 hours ago

Moonrise Hotel
4.0-star property

Moonrise Hotel

9/10 Wonderful! (2,013 reviews)

Sep 17 - Sep 20

3 night stay

Chicago (CHI) to St. Louis (STL)

Southwest Airlines • Coach

St. Louis (STL) to Chicago (CHI)

American Airlines • Coach
Price was $712, price is now $581 per person
$581
per person
found 17 hours ago

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More About Flying To Rolla from Chicago

Route Information for Flights from Chicago to Rolla

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

Chicago to Rolla

Orbitz is the best place to find guaranteed low prices on Chicago to Rolla flights. Because of our cutting-edge mobile tools and low fares on domestic and international flights, Orbitz is the best starting point for travelers.

Find Cheap Chicago to Rolla Flights

Orbitz offers free mobile apps for iPhone and Android devices—a great way to find fantastic deals on flights from Chicago to Rolla. Not only that, but you can check the status of your flight or even book low cost hotel rooms with the apps or on m.orbitz.com.

Get Miles and Points for Your Flight

Simply enter your frequent flyer information while booking to get miles or points for qualifying Chicago to Rolla flights. This information can all be saved in your Orbitz account, which means it will not have to be entered each time you take advantage of a great air fare deal.

Flight Alerts Take Away the Stress

Orbitz does not want travelers to worry on their flights from Chicago to Rolla. We keep you updated on any flight changes for Chicago to Rolla flights with alerts sent directly to your email or a mobile device. These alerts can also be sent to friends and family.

Discount Travel Planning Made Simple

You will have no problems finding budget flights from Chicago to Rolla on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.

Frequently asked questions

Are there non-stop flights from Chicago to Rolla?
Get ready to book, because there are two carriers that operate nonstop flights from O'Hare Airport to STL. Lock in a great deal with United Airlines or American Airlines.
What is the shortest flight from Chicago to Rolla?
It can be as a short and sweet as 1 hour and 9 minutes. If you're a firm believer that your vacation hours should be spent 'vacationing' instead of flying, you'll enjoy the journey from Chicago to Rolla.
What airlines fly from Chicago to Rolla most frequently?
Consider booking a flight with United Airlines (UA), which frequently services this route. This airline offers 212 flights every month between Chicago, IL (ORD-O'Hare Intl.) and Lambert Field. Alternatively, book a seat with American Airlines (AA). You'll have 165 monthly flights between Chicago and Rolla to choose from with this company.
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.

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.