$69 Cheap flight deals from Chicago (CHI) to Monroeville (PIT)

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This Weekend's Flight Deals from Chicago to Monroeville

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, Jul 26 - Thu, Jul 30
ORD
O'Hare Intl.
PIT
Pittsburgh Intl.
$400 Roundtrip, found 4 days ago
$400
Roundtrip
found 4 days ago
Select Sun Country Airlines flight, departing Sun, Jul 26 from O'Hare Intl. to Pittsburgh Intl., returning Thu, Jul 30, priced at $400 found 4 days ago
Sat, Jul 25 - Mon, Jul 27
MDW
Midway Intl.
PIT
Pittsburgh Intl.
$527 Roundtrip, found 15 hours ago
$527
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sat, Jul 25 from Midway Intl. to Pittsburgh Intl., returning Mon, Jul 27, priced at $527 found 15 hours ago
Fri, Jul 24 - Sun, Jul 26
RFD
Greater Rockford
PIT
Pittsburgh Intl.
$555 Roundtrip, found 2 days ago
$555
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jul 24 from Greater Rockford to Pittsburgh Intl., returning Sun, Jul 26, priced at $555 found 2 days ago

Airfares from $69 One Way, $137 Round Trip from Chicago to Monroeville

Prices starting at $137 for return flights and $69 for one-way flights to Monroeville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Oct 12 - Tue, Oct 13
MDW
Chicago
PIT
Pittsburgh
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Oct 12 from Chicago to Pittsburgh, returning Tue, Oct 13, priced at $137 found 1 day ago
Mon, Oct 12 - Tue, Oct 13
ORD
Chicago
PIT
Pittsburgh
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Oct 12 from Chicago to Pittsburgh, returning Tue, Oct 13, priced at $137 found 1 day ago
Sat, Sep 12 - Mon, Sep 14
ORD
Chicago
PIT
Pittsburgh
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 12 from Chicago to Pittsburgh, returning Mon, Sep 14, priced at $140 found 2 days ago
Thu, Oct 8 - Tue, Oct 13
ORD
Chicago
PIT
Pittsburgh
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Oct 8 from Chicago to Pittsburgh, returning Tue, Oct 13, priced at $147 found 1 day ago
Mon, Oct 12 - Tue, Oct 13
ORD
Chicago
PIT
Pittsburgh
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Oct 12 from Chicago to Pittsburgh, returning Tue, Oct 13, priced at $157 found 1 day ago

Monroeville economy flight packages

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
2.0-star property

Stay Pittsburgh

8/10 Very Good! (302 reviews)

Sep 11 - Sep 14

3 night stay

Chicago (ORD) to Pittsburgh (PIT)

United • Roundtrip • Coach
Save 100% on your flight
Price was $515, price is now $363 per person
$363
per person
found 1 day ago
I traveled to Pittsburgh for a Pirates game with a friend back in June. This place was perfect for us. We rented 3D. It was a clean, a two bedroom, two bath apartment, and six twin beds with an easy 15-minute walk to the PNC Park. Crossing the Roberto Clemente bridge was a blast with all the fans. Also Stay Pittsburgh is walking distance to the Monongahela Incline (drops you off in Mount Washington) and the Market Square where I relaxed with a Primanti Bros sandwich. The price was way better than a single hotel room. Truth be told it’s not a Ritz Carlton but like I said it’s walking distance to everything. Some issues we experienced – their “About this property” promotes Street parking available, so we thought FREE street parking. This is not the case, just an FYI you can park on the street but it’s very expensive. They should update their “About this property” to state PAID street parking available or state there are many parking garages in the area that you can park for $25-$30 dollars a night which is not bad but people should know. Although the place is clean, and an awesome location, things like the towels and pots and pans seem like they are from the 1970s. Also, some aging towel racks and faucets. I didn’t mind just something you should beware. Overall, if I ever return to Pittsburgh I would definitely stay there again even with my wife, of course with an apartment that does not have twin beds. Remember location, location, location is key!

Reviewed on Jul 13, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
4.0-star property

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

8.4/10 Very Good! (1,078 reviews)

Sep 11 - Sep 14

3 night stay

Chicago (ORD) to Pittsburgh (PIT)

United • Roundtrip • Coach
Save 100% on your flight
Price was $877, price is now $645 per person
$645
per person
found 1 day ago

Crowne Plaza Suites Pittsburgh South by IHG
3.5-star property

Crowne Plaza Suites Pittsburgh South by IHG

8.8/10 Excellent! (1,000 reviews)

Sep 11 - Sep 14

3 night stay

Chicago (ORD) to Pittsburgh (PIT)

United • Roundtrip • Coach
Price was $569, price is now $429 per person
$429
per person
found 1 day ago
Location was great!

Reviewed on Jul 17, 2026

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More About Flying To Monroeville from Chicago

Route Information for Flights from Chicago to Monroeville

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

Chicago to Monroeville

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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.