$167 Cheap flight deals from Youngstown (BFP) to Chicago (CHI)

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Airfares from $167 One Way, $249 Round Trip from Youngstown to Chicago

Prices starting at $249 for return flights and $167 for one-way flights to Chicago 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, Sep 4 - Sat, Sep 5
CAK
Akron
ORD
Chicago
$249 Roundtrip, found 3 days ago
$249
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Sep 4 from Akron to Chicago, returning Sat, Sep 5, priced at $249 found 3 days ago
Fri, Aug 21 - Sun, Aug 23
CAK
Akron
ORD
Chicago
$249 Roundtrip, found 3 days ago
$249
Roundtrip
found 3 days ago
Select United flight, departing Fri, Aug 21 from Akron to Chicago, returning Sun, Aug 23, priced at $249 found 3 days ago
Fri, Aug 14 - Sun, Aug 16
CAK
Akron
RFD
Rockford
$252 Roundtrip, found 6 days ago
$252
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Aug 14 from Akron to Rockford, returning Sun, Aug 16, priced at $252 found 6 days ago
Tue, Jul 28 - Mon, Aug 3
CAK
Akron
ORD
Chicago
$255 Roundtrip, found 5 days ago
$255
Roundtrip
found 5 days ago
Select United flight, departing Tue, Jul 28 from Akron to Chicago, returning Mon, Aug 3, priced at $255 found 5 days ago
Fri, Aug 21 - Sun, Aug 23
CAK
Akron
ORD
Chicago
$257 Roundtrip, found 3 days ago
$257
Roundtrip
found 3 days ago
Select United flight, departing Fri, Aug 21 from Akron to Chicago, returning Sun, Aug 23, priced at $257 found 3 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile
4.0-star property

Chicago Marriott Downtown Magnificent Mile

8.8/10 Excellent! (1,006 reviews)

Aug 27 - Aug 29

2 night stay

Akron (CAK) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Price was $684, price is now $530 per person
$530
per person
found 22 hours ago
This hotel was in the heart of everything. The front desk person Stephan was truly AMAZING. Nice guy and was very accommodating and did it with a smile. Super guy!!!

Reviewed on Jul 8, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (4,586 reviews)

Aug 27 - Aug 29

2 night stay

Akron (CAK) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,018, price is now $735 per person
$735
per person
found 22 hours ago
There was not any microwave for reheating the food neither in the room nor in the restaurant.

Reviewed on Jul 11, 2026

Omni Chicago Hotel
4.5-star property

Omni Chicago Hotel

9.2/10 Wonderful! (1,819 reviews)

Aug 27 - Aug 29

2 night stay

Akron (CAK) to Chicago (ORD)

American Airlines • Non-stop roundtrip • Coach
Price was $881, price is now $648 per person
$648
per person
found 22 hours ago
Great location and a friendly staff made this a great experience. The rooms are very nice, but a little dated, which made it feel a little less clean. The staff was amazing, especially the doorman/bellman, Ham. He went out of his way help everytime we arrived or departed, he asked how our day was and offered directions. I really can’t speak highly enough of him. We didn’t utilize the restaurant while there, but I did visit the bar and they had an excellent selection of high end bourbons.

Reviewed on Jul 11, 2026

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More About Flying To Chicago from Youngstown

Route Information for Flights from Youngstown to Chicago

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

Youngstown to Chicago

Low Cost Flights From Youngstown to Chicago

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Planning your vacation has never been easier using the convenient Orbitz apps available for most mobile devices. If there are any changes or delays for Youngstown to Chicago flights, Orbitz customers receive instant free alerts via email or mobile phone text message. Change or cancel flights from Youngstown to Chicago anytime online or by calling our Customer Service representatives.

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Frequently asked questions

Am I able to catch a flight from Youngstown to Chicago now?
If you're puzzled about quarantine and travel restrictions when getting a flight from Youngstown to Chicago, go right to our Covid-19 Travel Advisor.
Are there non-stop flights from Youngstown to Chicago?
American Airlines and United Airlines fly direct from PIT to Chicago, IL Airport (ORD-O'Hare Intl.), which means you won't need to worry about swapping planes or waiting around during a stopover.
What is the shortest flight from Youngstown to Chicago?
It can zip by in as little as 2 hours and 17 minutes. If you strongly believe your vacation hours should be spent 'vacationing' rather than flying, you'll enjoy the trip from PIT to Midway Intl. Airport (MDW).
What airlines fly from Youngstown to Chicago most frequently?
There are a couple of airlines offering the most frequent flights from Pittsburgh Intl. Airport (PIT) to ORD, including American Airlines (AA). The preferred choice of many travelers, it operates 156 flights on this route every month. If you can't find the right flight for you there, look into the airfares with United Airlines (UA). This airline is a fantastic alternative and has 117 flights from Youngstown to Chicago each month.
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?
We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago with flexible change policies?
In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.
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 2020 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 the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.
How can I save money on flights?
To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

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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.