Pittsburgh (PIT) to Chicago (ORD), Nov 16, 2026: round trips from $255, one way from $135

Pittsburgh (PIT) to Chicago (ORD), Nov 16, 2026: round trips from $255, one way from $135 on Axel, checked Oct 29, 2026. Lowest published fares: $255 round trip, Axel-exclusive, American Airlines, nonstop, Nov 16–17, 2026; $135 one way, Axel-exclusive, American Airlines, nonstop, Nov 16, 2026; 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 Chicago for these trips

Hotels: under a trip, hotels in Chicago 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 Chicago for these nights (Nov 16–17, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $119 total · 4★ Warwick Allerton - Chicago, $109 total · 5★ Sofitel Chicago Magnificent Mile, $460 total
• Hotels in Chicago for these nights (Nov 16–18, 2026 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $228 total · 4★ Warwick Allerton - Chicago, $272 total · 5★ Sofitel Chicago Magnificent Mile, $909 total
• Hotels in Chicago for these nights (Nov 16–19, 2026 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $342 total · 4★ Warwick Allerton - Chicago, $396 total · 5★ Sofitel Chicago Magnificent Mile, $1,222 total
• Hotels in Chicago for these nights (Nov 16–20, 2026 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $450 total · 4★ Warwick Allerton - Chicago, $519 total · 5★ Sofitel Chicago Magnificent Mile, $1,536 total
• Hotels in Chicago for these nights (Nov 16–21, 2026 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $656 total · 4★ Hotel Lincoln, $771 total · 5★ Sofitel Chicago Magnificent Mile, $1,833 total
• Hotels in Chicago for these nights (Nov 16–22, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $854 total · 4★ Millennium Hotel Knickerbocker Chicago, $996 total · 5★ Sofitel Chicago Magnificent Mile, $2,086.50 total
• Hotels in Chicago for these nights (Nov 16–23, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $963 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,113 total · 5★ Sofitel Chicago Magnificent Mile, $2,296.50 total
• Hotels in Chicago for these nights (Nov 16–24, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,072 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,230 total · 5★ Sofitel Chicago Magnificent Mile, $2,506.50 total
• Hotels in Chicago for these nights (Nov 16–25, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,181 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,350 total · 5★ Sofitel Chicago Magnificent Mile, $2,709.50 total
• Hotels in Chicago for these nights (Nov 16–26, 2026 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,282 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,478 total · 5★ Sofitel Chicago Magnificent Mile, $2,919.50 total
• Hotels in Chicago for these nights (Nov 16–27, 2026 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,419 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,600 total · 5★ Sofitel Chicago Magnificent Mile, $3,118.50 total
• Hotels in Chicago for these nights (Nov 16–28, 2026 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,586 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,765 total · 5★ Sofitel Chicago Magnificent Mile, $3,421.50 total
• Hotels in Chicago for these nights (Nov 16–29, 2026 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,729 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,951 total · 5★ Sofitel Chicago Magnificent Mile, $3,718.50 total
• Hotels in Chicago for these nights (Nov 16–30, 2026 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,843 total · 4★ Millennium Hotel Knickerbocker Chicago, $2,112 total · 5★ Sofitel Chicago Magnificent Mile, $4,027.50 total

All hotels in Chicago

2026-11-16 · one way · Axel-exclusive $135.00

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.

2026-11-16 · one way · Axel-exclusive $160.00

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.

2026-11-16 → 2026-11-17 · Axel-exclusive $255.00

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA383: ORD 2026-11-17 18:17:00 → PIT 2026-11-17 20:57:00; nonstop; 100 minutes. Local airport times.

2026-11-16 → 2026-11-17 · Axel-exclusive $282.50

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA3484: ORD 2026-11-17 15:45:00 → PIT 2026-11-17 18:19:00; nonstop; 94 minutes. Local airport times.

2026-11-16 → 2026-11-18 · Axel-exclusive $255.00

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA3012: ORD 2026-11-18 17:00:00 → PIT 2026-11-18 19:43:00; nonstop; 103 minutes. Local airport times.

2026-11-16 → 2026-11-18 · Axel-exclusive $282.50

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA1946: ORD 2026-11-18 18:10:00 → PIT 2026-11-18 20:49:00; nonstop; 99 minutes. Local airport times.

2026-11-16 → 2026-11-19 · Axel-exclusive $255.00

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA2720: ORD 2026-11-19 17:54:00 → PIT 2026-11-19 20:36:00; nonstop; 102 minutes. Local airport times.

2026-11-16 → 2026-11-19 · Axel-exclusive $282.50

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA4535: ORD 2026-11-19 12:48:00 → PIT 2026-11-19 15:19:00; nonstop; 91 minutes. Local airport times.

2026-11-16 → 2026-11-20 · Axel-exclusive $255.00

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA383: ORD 2026-11-20 18:13:00 → PIT 2026-11-20 21:00:00; nonstop; 107 minutes. Local airport times.

2026-11-16 → 2026-11-20 · Axel-exclusive $282.50

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA3464: ORD 2026-11-20 21:30:00 → PIT 2026-11-20 23:59:00; nonstop; 89 minutes. Local airport times.

2026-11-16 → 2026-11-22 · Axel-exclusive $255.00

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA4757: ORD 2026-11-22 09:49:00 → PIT 2026-11-22 12:34:00; nonstop; 105 minutes. Local airport times.

2026-11-16 → 2026-11-22 · Axel-exclusive $282.50

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA1946: ORD 2026-11-22 18:23:00 → PIT 2026-11-22 21:02:00; nonstop; 99 minutes. Local airport times.

2026-11-16 → 2026-11-23 · Axel-exclusive $255.00

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA4363: ORD 2026-11-23 21:00:00 → PIT 2026-11-23 23:44:00; nonstop; 104 minutes. Local airport times.

2026-11-16 → 2026-11-23 · Axel-exclusive $282.50

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA5611: ORD 2026-11-23 06:59:00 → PIT 2026-11-23 09:30:00; nonstop; 91 minutes. Local airport times.

2026-11-16 → 2026-11-24 · Axel-exclusive $299.63

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA3049: ORD 2026-11-24 16:59:00 → PIT 2026-11-24 19:43:00; nonstop; 104 minutes. Local airport times.

2026-11-16 → 2026-11-24 · Axel-exclusive $328.88

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA1349: ORD 2026-11-24 14:16:00 → PIT 2026-11-24 16:55:00; nonstop; 99 minutes. Local airport times.

2026-11-16 → 2026-11-26 · Axel-exclusive $299.63

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA2720: ORD 2026-11-26 17:54:00 → PIT 2026-11-26 20:36:00; nonstop; 102 minutes. Local airport times.

2026-11-16 → 2026-11-26 · Axel-exclusive $328.88

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA1349: ORD 2026-11-26 14:16:00 → PIT 2026-11-26 16:55:00; nonstop; 99 minutes. Local airport times.

2026-11-16 → 2026-11-27 · Axel-exclusive $299.63

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA383: ORD 2026-11-27 18:13:00 → PIT 2026-11-27 21:00:00; nonstop; 107 minutes. Local airport times.

2026-11-16 → 2026-11-27 · Axel-exclusive $328.88

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA1349: ORD 2026-11-27 14:16:00 → PIT 2026-11-27 16:55:00; nonstop; 99 minutes. Local airport times.

2026-11-16 → 2026-11-28 · Axel-exclusive $299.63

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA3049: ORD 2026-11-28 16:59:00 → PIT 2026-11-28 19:43:00; nonstop; 104 minutes. Local airport times.

2026-11-16 → 2026-11-28 · Axel-exclusive $328.88

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA4549: ORD 2026-11-28 15:55:00 → PIT 2026-11-28 18:40:00; nonstop; 105 minutes. Local airport times.

2026-11-16 → 2026-11-30 · Axel-exclusive $299.63

• American Airlines AA2644: PIT 2026-11-16 08:02:00 → ORD 2026-11-16 09:06:00; nonstop; 124 minutes. Local airport times.
• American Airlines AA4363: ORD 2026-11-30 21:00:00 → PIT 2026-11-30 23:44:00; nonstop; 104 minutes. Local airport times.

2026-11-16 → 2026-11-30 · Axel-exclusive $328.88

• United Airlines UA1317 / UA2497: PIT 2026-11-16 15:15:00 → ORD 2026-11-16 19:05:00; 1 stop(s) via IAD; 290 minutes. Local airport times.
  • UA1317: PIT 2026-11-16 15:15:00 → IAD 2026-11-16 16:20:00; layover at IAD: 79 minutes.
  • UA2497: IAD 2026-11-16 17:39:00 → ORD 2026-11-16 19:05:00.
• United Airlines UA3465: ORD 2026-11-30 07:25:00 → PIT 2026-11-30 10:04:00; nonstop; 99 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 15, 2026 · Return options
• Nov 17, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Pittsburgh (PIT) to Chicago (ORD) · Nov 16, 2026 · 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 Chicago 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.
• Next: each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Search flights and hotels with your AI assistant · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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