Cheap Flight Deals From Pittsburgh (PIT) to Chicago (CHI) Starting at $79

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This Weekend's Flight Deals from Pittsburgh 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.

Sun, Sep 24 - Thu, Sep 28
PIT
Pittsburgh Intl.
ORD
O'Hare Intl.
$358 Roundtrip, found 1 day ago
$358
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Sep 24 from Pittsburgh Intl. to O'Hare Intl., returning Thu, Sep 28, priced at $358 found 1 day ago
Sat, Sep 23 - Mon, Sep 25
PIT
Pittsburgh Intl.
MDW
Midway Intl.
$571 Roundtrip, found 1 day ago
$571
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 23 from Pittsburgh Intl. to Midway Intl., returning Mon, Sep 25, priced at $571 found 1 day ago

Airfares from $79 One Way, $154 Round Trip from Pittsburgh to Chicago

Prices starting at $154 for return flights and $79 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.

Sat, Oct 28 - Sun, Oct 29
PIT
Pittsburgh
ORD
Chicago
$154 Roundtrip, found 5 days ago
$154
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, Oct 28 from Pittsburgh to Chicago, returning Sun, Oct 29, priced at $154 found 5 days ago
Wed, Nov 8 - Sat, Nov 11
PIT
Pittsburgh
ORD
Chicago
$156 Roundtrip, found 3 days ago
$156
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Nov 8 from Pittsburgh to Chicago, returning Sat, Nov 11, priced at $156 found 3 days ago
Sat, Oct 14 - Sat, Oct 21
PIT
Pittsburgh
ORD
Chicago
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, Oct 14 from Pittsburgh to Chicago, returning Sat, Oct 21, priced at $157 found 3 hours ago
Thu, Oct 19 - Thu, Oct 26
PIT
Pittsburgh
ORD
Chicago
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Oct 19 from Pittsburgh to Chicago, returning Thu, Oct 26, priced at $158 found 1 day ago
Sat, Oct 28 - Sun, Oct 29
PIT
Pittsburgh
ORD
Chicago
$158 Roundtrip, found 5 days ago
$158
Roundtrip
found 5 days ago
Select United flight, departing Sat, Oct 28 from Pittsburgh to Chicago, returning Sun, Oct 29, priced at $158 found 5 days ago

Chicago economy flight packages

Courtyard by Marriott Chicago Magnificent Mile
3.0-star property

Courtyard by Marriott Chicago Magnificent Mile

8.4/10 Very Good! (1,004 reviews)

Nov 16 - Nov 18

2 night stay

Pittsburgh (PIT) to Chicago (ORD)

United • Roundtrip • Coach
Price was $514, price is now $431 per person
per person
Clean, centrally located to many attractions.

Reviewed on Aug 5, 2023

Aloft Chicago Downtown River North
3.5-star property

Aloft Chicago Downtown River North

9.2/10 Wonderful! (1,003 reviews)

Nov 16 - Nov 18

2 night stay

Pittsburgh (PIT) to Chicago (ORD)

United • Roundtrip • Coach
Price was $502, price is now $426 per person
per person
I travel often and meet lots of hospitality staff but I must say the service received by the team here was stellar!! One team member in particular Thomas Chato was outstanding. He was attentive, informed, had many great suggestions and was overall super pleasant. His warm welcome was my very first impression of this hotel and it created a feeling of “making the right choice” as there are many hotel options in the area. Thomas’ attention to detail and strong listening skills helped us get to all the places we wanted to go and even assisted us with exploring new places I had never been to before in Chicago. He was super knowledgeable and solution oriented as many of the times hotel staff members lead with the “no’s” and not the “yes we can do that for you” Thomas Chato thank you for making this Chicago visit one to remember!!

Reviewed on Sep 20, 2023

Chicago Athletic Association, a Hyatt Hotel
4.5-star property

Chicago Athletic Association, a Hyatt Hotel

9/10 Wonderful! (1,001 reviews)

Nov 16 - Nov 18

2 night stay

Pittsburgh (PIT) to Chicago (ORD)

United • Roundtrip • Coach
Price was $565, price is now $487 per person
per person
An incredible, unique property- gorgeous atmosphere, fantastic views, amazing restaurants, comfortable accommodations, lovely staff

Reviewed on Jul 7, 2023

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Prices and availability subject to change. Additional terms may apply.

More About Flying To Chicago from Pittsburgh

Route Information for Flights from Pittsburgh to Chicago

Origin Airport IATA Code
PIT
Destination Airport IATA Code
CHI
Distance
410 mi
Direct Flight Airlines
American Airlines, Qatar Airways, Air Canada, JAL, Aer Lingus, Emirates, SWISS, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Royal Jordanian, SAS, ANA, Lufthansa, Gulf Air, British Airways
Earliest Flight Arrival
11:40AM UTC
Latest Flight Arrival
10:54PM UTC

Book Your Flight from Pittsburgh to Chicago

Pittsburgh International Airport

The Pittsburgh International Airport is located just twenty miles west of downtown on Airport Boulevard. Twelve airlines service the airport, including Midwest, Northwest, JetBlue, Delta, Continental and American Airlines. Orbitz.com can locate both domestic and international flights from Pittsburgh for the budget traveler.

Parking at the Airport

Short-term, long-term and extended parking lots are available at the airport. Rates are charged by the hour or by the day. Valet parking is also available for an additional fee. The short-term lot is perfect for people who are dropping off or picking up travelers. Long-term lots are ideal for travelers going on short vacations, and the extended lots are most economical for long business trips. Shuttle services are available to and from the parking lots.

Transportation to the Airport

Getting to the airport can often be a challenge. Orbitz.com can help you select a car rental service if you want to rent a car during your stay. Most hotels offer their guests free shuttle service to and from the airport. Limos are available for rent, and fees are usually charged by the hour. Other transportation options include metered taxi services and the city bus system, which charges a flat rate.

Pittsburgh International Airport Restaurants

Travelers can enjoy a meal or a snack in the airport terminals before they board their plane. Restaurant choices include McDonald's, which offers a variety of breakfast items and coffee, and Mayorga Coffee Roasters, which offers a selection of gourmet coffees and pastries. Orbitz.com can help with dining options while providing low-fare flights from Pittsburgh for people traveling on a budget.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Frequently asked questions

Am I able to catch a flight from Pittsburgh to Chicago now?
Go right to our Covid-19 Travel Advisor for the most up-to-date information on quarantine and travel restrictions when catching a flight from Pittsburgh to Chicago.
Are there non-stop flights from Pittsburgh to Chicago?
There most certainly are, which is terrific news if you’re not a huge fan of switching planes en route. American Airlines and United Airlines operate direct flights from PIT to O’Hare Airport.
What is the shortest flight from Pittsburgh to Chicago?
The trip from Pittsburgh to Chicago can be as quick as 1 hour and 32 minutes. With a short and sweet flight time like this, why not grab some friends and organize a spontaneous getaway?
What airlines fly from Pittsburgh to Chicago most frequently?
Check out American Airlines (AA). This airline offers some of the most frequent flights from PIT to O’Hare Airport. It operates 165 services on this route every month and is a favorite with travelers. If you’d like more options, check out the price of tickets with United Airlines (UA), which has 152 flights from Pittsburgh to Chicago every 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 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.

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.