$165 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, Aug 15 - Mon, Aug 18
CAK
Akron-Canton
ORD
O'Hare Intl.
$272 Roundtrip, found 2 days ago
$272
Roundtrip
found 2 days ago
Select United flight, departing Fri, Aug 15 from Akron-Canton to O'Hare Intl., returning Mon, Aug 18, priced at $272 found 2 days ago

Airfares from $165 One Way, $189 Round Trip from Youngstown to Chicago

Prices starting at $189 for return flights and $165 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, Oct 24 - Mon, Oct 27
CAK
Akron
ORD
Chicago
$189 Roundtrip, found 4 days ago
$189
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Oct 24 from Akron to Chicago, returning Mon, Oct 27, priced at $189 found 4 days ago
Thu, Aug 28 - Mon, Sep 1
CAK
Akron
ORD
Chicago
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Select United flight, departing Thu, Aug 28 from Akron to Chicago, returning Mon, Sep 1, priced at $192 found 4 days ago
Fri, Oct 24 - Mon, Oct 27
CAK
Akron
RFD
Rockford
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Oct 24 from Akron to Rockford, returning Mon, Oct 27, priced at $192 found 4 days ago
Fri, Oct 24 - Mon, Oct 27
CAK
Akron
ORD
Chicago
$194 Roundtrip, found 4 days ago
$194
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Oct 24 from Akron to Chicago, returning Mon, Oct 27, priced at $194 found 4 days ago
Thu, Aug 28 - Mon, Sep 1
CAK
Akron
ORD
Chicago
$196 Roundtrip, found 4 days ago
$196
Roundtrip
found 4 days ago
Select United flight, departing Thu, Aug 28 from Akron to Chicago, returning Mon, Sep 1, priced at $196 found 4 days ago

Chicago economy flight packages

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

citizenM Chicago Downtown

9.2/10 Wonderful! (3,522 reviews)

Sep 15 - Sep 18

3 night stay

Akron (CAK) to Chicago (ORD)

United • Coach

Chicago (ORD) to Akron (CAK)

American Airlines • Coach
per person
found 11 hours ago
Nice, staff, good location

Reviewed on Jun 22, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,679 reviews)

Sep 15 - Sep 18

3 night stay

Akron (CAK) to Chicago (ORD)

United • Coach

Chicago (ORD) to Akron (CAK)

American Airlines • Coach
Save 100% on your flight
per person
found 11 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,000 reviews)

Sep 15 - Sep 18

3 night stay

Akron (CAK) to Chicago (ORD)

United • Coach

Chicago (ORD) to Akron (CAK)

American Airlines • Coach
Save 100% on your flight
per person
found 11 hours ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

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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
342 mi
Direct Flight Airlines
Avianca, Lufthansa, Air New Zealand, United Airlines
Earliest Flight Arrival
11:46AM UTC
Latest Flight Arrival
10:36PM UTC

Youngstown to Chicago

Looking for cheap Youngstown to Chicago flights? Orbitz has the cheapest air fares for flights from Youngstown to Chicago. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.

Mobile Deals and Steals

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Book Hotels With Confidence

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Access Your Flight Information Anytime

Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Youngstown to Chicago flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Youngstown to Chicago on your mobile device too, including delays and baggage claim details.

Cheap Air Ticket Prices Guaranteed

Orbitz is your number one source for low fares for Youngstown to Chicago flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Chicago. Need hotels too? You can book them last minute on your mobile phone.

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!

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.