$133 Cheap flight deals from Youngstown (BFP) to Chicago (CHI)

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This Weekend's Flight Deals from Youngstown to Chicago

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 - Mon, Apr 13
CAK
Akron-Canton
RFD
Greater Rockford
$368 Roundtrip, found 6 hours ago
$368
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Fri, Apr 10 from Akron-Canton to Greater Rockford, returning Mon, Apr 13, priced at $368 found 6 hours ago
Fri, Apr 10 - Mon, Apr 13
CAK
Akron-Canton
ORD
O'Hare Intl.
$372 Roundtrip, found 6 hours ago
$372
Roundtrip
found 6 hours ago
Select United flight, departing Fri, Apr 10 from Akron-Canton to O'Hare Intl., returning Mon, Apr 13, priced at $372 found 6 hours ago

Airfares from $133 One Way, $249 Round Trip from Youngstown to Chicago

Prices starting at $249 for return flights and $133 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.

Wed, Jun 10 - Sun, Jun 14
CAK
Akron
ORD
Chicago
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jun 10 from Akron to Chicago, returning Sun, Jun 14, priced at $249 found 1 day ago
Sat, Jun 13 - Thu, Jun 18
CAK
Akron
ORD
Chicago
$254 Roundtrip, found 3 days ago
$254
Roundtrip
found 3 days ago
Select United flight, departing Sat, Jun 13 from Akron to Chicago, returning Thu, Jun 18, priced at $254 found 3 days ago
Wed, Jun 10 - Sun, Jun 14
CAK
Akron
ORD
Chicago
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jun 10 from Akron to Chicago, returning Sun, Jun 14, priced at $257 found 1 day ago
Sat, Apr 18 - Sun, Apr 19
CAK
Akron
RFD
Rockford
$257 Roundtrip, found 6 days ago
$257
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Apr 18 from Akron to Rockford, returning Sun, Apr 19, priced at $257 found 6 days ago
Wed, Apr 22 - Sat, Apr 25
CAK
Akron
ORD
Chicago
$260 Roundtrip, found 5 days ago
$260
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 22 from Akron to Chicago, returning Sat, Apr 25, priced at $260 found 5 days ago

Chicago first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont
3.0-star property

Sonesta Chicago O'Hare Airport Rosemont

8.6/10 Excellent! (1,717 reviews)

May 17 - May 20

3 night stay

Akron (CAK) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $911, price is now $818 per person
$818
per person
found 11 hours ago
Room was excellent, clean and comfortable. Staff was freindly and helpful.

Reviewed on Jan 16, 2026

Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.4/10 Very Good! (2,231 reviews)

May 17 - May 20

3 night stay

Akron (CAK) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,205, price is now $1,088 per person
$1,088
per person
found 11 hours ago
This place gets 3 stars from me only due to its great location. It's in rather poor repair and its overall appearance and upkeep do not reflect well on the Hilton brand. It seems clear that property ownership are not bothering to put money into it because they know they will get traffic from the airport.

Reviewed on Feb 25, 2026

Hilton Rosemont Chicago O'Hare
3.5-star property

Hilton Rosemont Chicago O'Hare

8.4/10 Very Good! (1,001 reviews)

May 17 - May 20

3 night stay

Akron (CAK) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,097, price is now $1,005 per person
$1,005
per person
found 11 hours ago
Good hotel close to airport, with free airport shuttle, 7-10 min away. Quite convenient

Reviewed on Nov 4, 2025

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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

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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.