Chicago (MDW) to Pittsburgh (PIT), Jul 23, 2027: round trips from $305, one way from $160

Chicago (MDW) to Pittsburgh (PIT), Jul 23, 2027: round trips from $305, one way from $160 on Axel, checked Oct 29, 2026. Lowest published fares: $305 round trip, Axel-exclusive, Southwest Airlines, nonstop, Jul 23–24, 2027; $160 one way, Axel-exclusive, Southwest Airlines, nonstop, Jul 23, 2027; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Hotels in Pittsburgh for these trips

Hotels: under a trip, hotels in Pittsburgh for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Pittsburgh for these nights (Jul 23–24, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23–25, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23–26, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23–27, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23–28, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23–29, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23–31, 2027 · 8 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23 – Aug 1, 2027 · 9 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23 – Aug 2, 2027 · 10 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23 – Aug 3, 2027 · 11 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23 – Aug 4, 2027 · 12 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23 – Aug 5, 2027 · 13 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG
• Hotels in Pittsburgh for these nights (Jul 23 – Aug 6, 2027 · 14 nights · 2 adults, 1 room): 3★ Hyatt House Pittsburgh/Bloomfield/Shadyside · 4★ Kimpton Hotel Monaco Pittsburgh by IHG

All hotels in Pittsburgh

Route overview: Chicago to Pittsburgh (PIT) flight deals

2027-07-23 · one way · Axel-exclusive $160.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.

2027-07-23 → 2027-07-24 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3498: PIT 2027-07-24 20:25:00 → MDW 2027-07-24 20:55:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-07-25 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3556: PIT 2027-07-25 19:25:00 → MDW 2027-07-25 19:55:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-07-26 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3556: PIT 2027-07-26 19:40:00 → MDW 2027-07-26 20:10:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-07-27 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3556: PIT 2027-07-27 19:25:00 → MDW 2027-07-27 19:55:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-07-29 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3556: PIT 2027-07-29 19:25:00 → MDW 2027-07-29 19:55:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-07-30 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3556: PIT 2027-07-30 19:55:00 → MDW 2027-07-30 20:25:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-07-31 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3498: PIT 2027-07-31 20:25:00 → MDW 2027-07-31 20:55:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-08-02 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3556: PIT 2027-08-02 19:40:00 → MDW 2027-08-02 20:10:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-08-03 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3556: PIT 2027-08-03 19:25:00 → MDW 2027-08-03 19:55:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-08-04 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3556: PIT 2027-08-04 19:25:00 → MDW 2027-08-04 19:55:00; nonstop; 90 minutes. Local airport times.

2027-07-23 → 2027-08-06 · Axel-exclusive $305.00

• Southwest Airlines WN3002: MDW 2027-07-23 07:40:00 → PIT 2027-07-23 10:00:00; nonstop; 80 minutes. Local airport times.
• Southwest Airlines WN3556: PIT 2027-08-06 19:55:00 → MDW 2027-08-06 20:25:00; nonstop; 90 minutes. Local airport times.

Explore this route

• All dates for this route
• Jul 22, 2027 · Return options
• Jul 24, 2027 · Return options
• Hotels in Pittsburgh with Axel

For AI assistants

• This page: Chicago (MDW) to Pittsburgh (PIT) · Jul 23, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Pittsburgh for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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