Flights from Chicago O'Hare

Curated weekend trip ideas. Prices are indicative from recent updates — verify availability before booking.

Last synced: Thu 07:00

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SortPrice Freshness ScoreViewBest per destination All dates

SourceAll Amadeus Aviasales

StopsDirect 1 stop 2+ stops All

AirlineAll AA AV B6 CM CX EK F9 IB SK TK UA VB Y4

Showing 12 deals • Airline filter: AA (out of 50 total deals)

ORD → Philadelphia (PHL)

2026-07-07 → 2026-07-16 • Direct • 3h

[Out: Tue 10:00 → Tue 13:00 • 3h] — [Stay: 8d 20h] — [Back: Thu 09:15 → Thu 12:15 • 3h]

AASource: Aviasales (cached)

See more dates for PHL• Inserted 2026-06-04 · Thu 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 175

Updated ~1h agoExpires in ~2d

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ORD → TUL

2026-09-15 → 2026-09-29 • Direct • 3h

[Out: Wed 03:30 → Wed 06:30 • 3h] — [Stay: 13d 9h] — [Back: Tue 15:47 → Tue 18:47 • 3h]

AASource: Aviasales (cached)

See more dates for TUL• Inserted 2026-06-04 · Thu 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 250

Updated ~1h agoExpires in ~2d

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ORD → YMQ

2026-08-24 → 2026-09-08 • Direct • 3h

[Out: Mon 13:18 → Mon 16:18 • 3h] — [Stay: 15d 5h] — [Back: Tue 21:34 → Wed 24:34 • 3h]

AASource: Aviasales (cached)

See more dates for YMQ• Inserted 2026-06-04 · Thu 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 282

Updated ~1h agoExpires in ~2d

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ORD → San Juan (SJU)

2026-08-16 → 2026-08-21 • Direct • 3h

[Out: Sun 22:20 → Mon 01:20 • 3h] — [Stay: 4d 4h] — [Back: Fri 04:55 → Fri 07:55 • 3h]

AASource: Aviasales (cached)

See more dates for SJU• Inserted 2026-06-04 · Thu 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 282

Updated ~1h agoExpires in ~2d

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ORD → Calgary (YYC)

2026-08-22 → 2026-09-03 • Direct • 3h

[Out: Sun 01:46 → Sun 04:46 • 3h] — [Stay: 11d 8h] — [Back: Thu 13:00 → Thu 16:00 • 3h]

AASource: Aviasales (cached)

See more dates for YYC• Inserted 2026-06-04 · Thu 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 304

Updated ~1h agoExpires in ~2d

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ORD → Baltimore (BWI)

2026-07-01 → 2026-07-04 • Direct • 3h

[Out: Wed 11:50 → Wed 14:50 • 3h] — [Stay: 2d 21h] — [Back: Sat 11:35 → Sat 14:35 • 3h]

AASource: Aviasales (cached)

See more dates for BWI• Inserted 2026-06-03 · Wed 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 305

Updated ~25h agoExpires in ~22h

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ORD → Charlotte (CLT)

2026-07-03 → 2026-07-06 • Direct • 3h

[Out: Fri 10:10 → Fri 13:10 • 3h] — [Stay: 3d 4h] — [Back: Mon 17:05 → Mon 20:05 • 3h]

AASource: Aviasales (cached)

See more dates for CLT• Inserted 2026-06-04 · Thu 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 315

Updated ~1h agoExpires in ~2d

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ORD → BUF

2026-12-24 → 2026-12-26 • Direct • 3h

[Out: Fri 01:55 → Fri 04:55 • 3h] — [Stay: 1d 7h] — [Back: Sat 12:00 → Sat 15:00 • 3h]

AASource: Aviasales (cached)

See more dates for BUF• Inserted 2026-06-03 · Wed 18:00• Synced 2026-06-04 · Thu 07:00

Est. USD 406

Updated ~13h agoExpires in ~1d

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ORD → YQB

2026-07-18 → 2026-08-08 • Direct • 3h

[Out: Sat 14:15 → Sat 17:15 • 3h] — [Stay: 21d 1h] — [Back: Sat 17:56 → Sat 20:56 • 3h]

AASource: Aviasales (cached)

See more dates for YQB• Inserted 2026-06-03 · Wed 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 427

Updated ~25h agoExpires in ~2d

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ORD → LSE

2026-08-22 → 2026-08-24 • Direct • 3h

[Out: Sat 15:30 → Sat 18:30 • 3h] — [Stay: 1d 22h] — [Back: Mon 16:57 → Mon 19:57 • 3h]

AASource: Aviasales (cached)

See more dates for LSE• Inserted 2026-06-03 · Wed 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 436

Updated ~25h agoExpires in ~22h

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ORD → ASE

2026-08-04 → 2026-08-09 • Direct • 3h

[Out: Tue 16:10 → Tue 19:10 • 3h] — [Stay: 4d 18h] — [Back: Sun 13:00 → Sun 16:00 • 3h]

AASource: Aviasales (cached)

See more dates for ASE• Inserted 2026-06-03 · Wed 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 540

Updated ~25h agoExpires in ~22h

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ORD → MKC

2026-06-13 → 2026-06-14 • Direct • 3h

[Out: Sun 03:30 → Sun 06:30 • 3h] — [Stay: 8h] — [Back: Sun 14:10 → Sun 17:10 • 3h]

AASource: Aviasales (cached)

See more dates for MKC• Inserted 2026-06-03 · Wed 06:00• Synced 2026-06-04 · Thu 07:00

Est. USD 708

Updated ~25h agoExpires in ~22h

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