Pittsburgh to Chicago: what the flight costs
In the last 60 days we checked this route 8 times. The typical return was £497 per person and the lowest £315, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £315 |
| Typical (median) | £497 |
| Price checks, 60 days | 8 |
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Trips we picked on this route
Just found · from PittsburghLowest in 30 daysWorth it, if
Chicago
16 – 18 Oct 2026 · 2 nights
- $418 per person, $241 below the typical fare on this route
- La Quinta in The Loop: 8 from 3,744 reviews, breakfast included
- Free cancellation at La Quinta, and Sunday's forecast is clear at 65°F
£1,242 for two · 2 nights · flights, hotel, taxes & fees
Flights £630 + hotel £612, taxes in · a checked bag each adds about £181
Frontier · with a stop · 13h
The catch: The Frontier fare has one stop and takes 13 hours overnight, landing at 7:51 AM Saturday, so you'll spend Friday's hotel night in transit.
Worth it if you'll trade a night of sleep for the lower fare; skip it if you want a nonstop and a full Friday evening in Chicago.
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| 15 Oct 2026 | 30 Oct – 1 Nov 2026 | £460 | UA | nonstop | 1h 48m | Kiwi.com |
| 15 Oct 2026 | 23 – 25 Oct 2026 | £548 | UA | nonstop | 1h 43m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £315 | Frontier | with a stop | 13h | Google Flights |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £525 | UA | nonstop | 1h 43m | Kiwi.com |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £468 | B6 + F9 + G4 | with a stop | 5h 54m | Kiwi.com |
| 13 Oct 2026 | 23 – 25 Oct 2026 | £531 | UA | nonstop | 1h 43m | Kiwi.com |
| 12 Oct 2026 | 23 – 25 Oct 2026 | £446 | UA | nonstop | 1h 43m | Kiwi.com |
| 12 Oct 2026 | 16 – 18 Oct 2026 | £531 | UA | nonstop | 1h 43m | Kiwi.com |
About Chicago
Chicago offers skyscraper architecture, a lakefront of beaches and parks, blues clubs, deep-dish pizza and museums of world rank.
Chicago from every city: when to go, where to stay, what to do
Questions about Pittsburgh to Chicago
What does a return from Pittsburgh to Chicago usually cost?
Over the last 60 days the typical price we found was £497 per person, taxes and fees included, across 8 checks; the lowest was £315.
When is the best time to fly from Pittsburgh to Chicago?
Chicago is at its best in May, June, July, August, September and October. Avoid December, January, February, March: Bitter cold and wind off the lake
Do I need a passport to fly from Pittsburgh to Chicago?
No passport needed for travellers from the United States: a government photo ID is enough for Chicago.
Prices converted from US dollars at the rate of 15 Oct 2026.