Southwest Airlines Pittsburgh to Chicago Roundtrip Flights

No special codes or coupons are required. Get these flight deals while available.

These Southwest Airlines flights on Expedia offer roundtrip airfares between Pittsburgh (PIT) and Chicago (MDW) for $77, nonstop. One-way options are available starting at $39. These are basic economy fares, and with Southwest, you can bring a personal item and a carry-on bag. The deal expires on January 31, 2026.

Travel is available on select dates:

• Departs PIT: Aug 13-14, 16, 18-21, 23, 25-28, 30; Sept 1-4, 6, 8-11, 13, 15-18, 20, 22-25, 27, 29-30; Oct 1-2, 4, 6-9, 11, 14-16, 18, 20-23, 25, 27-30; Nov 1, 3-6, 8, 10-13, 15, 17-20, 27; Dec 2-4, 6, 8-11, 13, 15-17; Jan 1, 6-8, 10, 12-15, 17, 19-22, 24, 26
• Departs MDW: Aug 13-14, 18-21, 23, 25-28, 30; Sept 1-4, 6, 8-11, 13, 15-18, 20, 22-25, 27, 29-30; Oct 1-2, 4, 6-9, 11, 13-16, 18, 20-23, 25, 27-30; Nov 1, 3-6, 8, 10-13, 15, 17-20; Dec 2-4, 6, 8-11, 13, 15-18; Jan 5-8, 10, 12-15, 17, 19-22, 24, 26