Flights from Chicago O'Hare

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

Last synced: Thu 06:00

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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 FI IB LO SK TK UA VB+1 more

Showing 48 destinations • From 61 matching deals

ORD → Fort Lauderdale (FLL)

2026-06-30 → 2026-07-22 • Direct • 3h 26m

[Out: Tue 12:52 → Tue 16:18 • 3h 26m] — [Stay: 21d 21h] — [Back: Wed 13:43 → Wed 17:09 • 3h 26m]

Source: Aviasales (cached)

See more dates for FLL• Inserted 2026-06-02 · Tue 07:00• Cached since 2026-06-02 · Tue 02:12• Synced 2026-06-04 · Thu 06:00

Est. USD 104

Cached ~47h agoExpires in ~1h

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ORD → ORL

2026-07-22 → 2026-07-28 • Direct • 3h 11m

[Out: Wed 22:13 → Thu 01:24 • 3h 11m] — [Stay: 6d] — [Back: Wed 24:59 → Wed 04:11 • 3h 12m]

Source: Aviasales (cached)

See more dates for ORL• Inserted 2026-06-03 · Wed 01:00• Cached since 2026-06-03 · Wed 24:19• Synced 2026-06-04 · Thu 06:00

Est. USD 116

Cached ~29h agoExpires in ~19h

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ORD → Los Angeles (LAX)

2026-07-08 → 2026-07-11 • Direct • 3h

[Out: Thu 02:13 → Thu 05:13 • 3h] — [Stay: 3d 2h] — [Back: Sun 06:59 → Sun 09:59 • 3h]

F9Source: Aviasales (cached)

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

Est. USD 120

Updated ~0h agoExpires in ~2d

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ORD → New York (NYC)

2026-08-07 → 2026-08-10 • Direct • 3h

[Out: Fri 14:39 → Fri 17:39 • 3h] — [Stay: 2d 17h] — [Back: Mon 11:05 → Mon 14:05 • 3h]

B6Source: Aviasales (cached)

See more dates for NYC• Inserted 2026-06-02 · Tue 18:00• Synced 2026-06-04 · Thu 06:00

Est. USD 143

Updated ~36h agoExpires in ~12h

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ORD → Houston (HOU)

2026-06-23 → 2026-06-24 • Direct • 3h

[Out: Tue 22:29 → Wed 01:29 • 3h] — [Stay: 1d 1h] — [Back: Thu 02:58 → Thu 05:58 • 3h]

F9Source: Aviasales (cached)

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

Est. USD 151

Updated ~24h agoExpires in ~24h

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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 06:00

Est. USD 175

Updated ~0h agoExpires in ~2d

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ORD → Phoenix (PHX)

2026-11-12 → 2026-11-16 • Direct • 3h 44m

[Out: Thu 22:00 → Fri 01:44 • 3h 44m] — [Stay: 4d 1h] — [Back: Tue 03:04 → Tue 06:48 • 3h 44m]

Source: Aviasales (cached)

See more dates for PHX• Inserted 2026-06-02 · Tue 07:00• Cached since 2026-06-02 · Tue 01:04• Synced 2026-06-04 · Thu 06:00

Est. USD 189

Cached ~47h agoExpires in ~1h

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ORD → Cleveland (CLE)

2026-07-01 → 2026-07-05 • Direct • 1h 25m

[Out: Thu 24:29 → Thu 01:54 • 1h 25m] — [Stay: 3d 8h] — [Back: Sun 10:04 → Sun 11:30 • 1h 26m]

Source: Aviasales (cached)

See more dates for CLE• Inserted 2026-06-02 · Tue 07:00• Cached since 2026-06-02 · Tue 03:44• Synced 2026-06-04 · Thu 06:00

Est. USD 222

Cached ~47h agoExpires in ~1h

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ORD → Washington (WAS)

2026-06-06 → 2026-06-08 • Direct • 3h

[Out: Sat 23:00 → Sun 02:00 • 3h] — [Stay: 1d 9h] — [Back: Mon 11:15 → Mon 14:15 • 3h]

UASource: Aviasales (cached)

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

Est. USD 227

Updated ~0h agoExpires in ~6h

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ORD → Mexico City (MEX)

2026-09-19 → 2026-10-04 • Direct • 3h

[Out: Sat 06:40 → Sat 09:40 • 3h] — [Stay: 14d 20h] — [Back: Sun 05:50 → Sun 08:50 • 3h]

Y4Source: Aviasales (cached)

See more dates for MEX• Inserted 2026-06-02 · Tue 18:00• Synced 2026-06-04 · Thu 06:00

Est. USD 245

Updated ~36h agoExpires in ~12h

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ORD → TUL

2026-09-15 → 2026-09-29 • Direct • 2h 3m

[Out: Wed 03:30 → Wed 05:33 • 2h 3m] — [Stay: 13d 10h] — [Back: Tue 15:47 → Tue 17:51 • 2h 4m]

Source: Aviasales (cached)

See more dates for TUL• Inserted 2026-06-04 · Thu 01:00• Cached since 2026-06-03 · Wed 23:39• Synced 2026-06-04 · Thu 06:00

Est. USD 250

Cached ~5h agoExpires in ~2d

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ORD → YMQ

2026-08-24 → 2026-09-08 • Direct • 2h 35m

[Out: Mon 13:18 → Mon 15:53 • 2h 35m] — [Stay: 15d 6h] — [Back: Tue 21:34 → Wed 24:09 • 2h 35m]

Source: Aviasales (cached)

See more dates for YMQ• Inserted 2026-06-04 · Thu 01:00• Cached since 2026-06-03 · Wed 22:14• Synced 2026-06-04 · Thu 06:00

Est. USD 282

Cached ~5h 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 06:00

Est. USD 282

Updated ~0h agoExpires in ~2d

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ORD → Baltimore (BWI)

2026-07-07 → 2026-07-09 • Direct • 3h

[Out: Wed 02:20 → Wed 05:20 • 3h] — [Stay: 1d 5h] — [Back: Thu 10:10 → Thu 13:10 • 3h]

UASource: Aviasales (cached)

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

Est. USD 286

Updated ~0h 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 06:00

Est. USD 304

Updated ~0h agoExpires in ~2d

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ORD → Cancún (CUN)

2026-07-04 → 2026-07-06 • Direct • 3h

[Out: Sat 11:00 → Sat 14:00 • 3h] — [Stay: 2d 2h] — [Back: Mon 16:00 → Mon 19:00 • 3h]

F9Source: Aviasales (cached)

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

Est. USD 310

Updated ~24h agoExpires in ~24h

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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 06:00

Est. USD 315

Updated ~0h agoExpires in ~2d

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ORD → Salt Lake City (SLC)

2026-06-11 → 2026-06-14 • Direct • 3h

[Out: Thu 17:40 → Thu 20:40 • 3h] — [Stay: 2d 15h] — [Back: Sun 11:10 → Sun 14:10 • 3h]

UASource: Aviasales (cached)

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

Est. USD 337

Updated ~24h agoExpires in ~18h

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ORD → MYR

2026-06-09 → 2026-06-16 • Direct • 3h

[Out: Tue 12:03 → Tue 15:03 • 3h] — [Stay: 7d 4h] — [Back: Tue 19:08 → Tue 22:08 • 3h]

UASource: Aviasales (cached)

See more dates for MYR• Inserted 2026-04-12 · Sun 06:00• Synced 2026-06-04 · Thu 06:00

Est. USD 345

Updated ~1272h agoExpires in ~18h

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ORD → FMY

2026-06-10 → 2026-06-16 • Direct • 3h

[Out: Wed 12:05 → Wed 15:05 • 3h] — [Stay: 6d 6h] — [Back: Tue 20:39 → Tue 23:39 • 3h]

UASource: Aviasales (cached)

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

Est. USD 348

Updated ~12h agoExpires in ~6h

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ORD → SRQ

2026-08-15 → 2026-08-22 • Direct • 3h 5m

[Out: Sat 16:10 → Sat 19:15 • 3h 5m] — [Stay: 7d 1h] — [Back: Sat 20:25 → Sat 23:31 • 3h 6m]

Source: Aviasales (cached)

See more dates for SRQ• Inserted 2026-06-02 · Tue 07:00• Cached since 2026-06-02 · Tue 02:30• Synced 2026-06-04 · Thu 06:00

Est. USD 377

Cached ~47h agoExpires in ~1h

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ORD → PWM

2026-08-15 → 2026-08-21 • Direct • 3h

[Out: Sun 24:13 → Sun 03:13 • 3h] — [Stay: 5d 10h] — [Back: Fri 13:08 → Fri 16:08 • 3h]

AASource: Aviasales (cached)

See more dates for PWM• Inserted 2026-03-03 · Tue 18:00• Synced 2026-06-04 · Thu 06:00

Est. USD 382

Updated ~2220h agoExpires in ~2d

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ORD → SYR

2026-06-18 → 2026-06-20 • Direct • 2h 8m

[Out: Thu 23:19 → Fri 01:27 • 2h 8m] — [Stay: 1d 9h] — [Back: Sat 10:10 → Sat 12:19 • 2h 9m]

Source: Aviasales (cached)

See more dates for SYR• Inserted 2026-06-04 · Thu 01:00• Cached since 2026-06-03 · Wed 23:52• Synced 2026-06-04 · Thu 06:00

Est. USD 385

Cached ~5h agoExpires in ~2d

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ORD → JAX

2026-06-18 → 2026-06-21 • Direct • 3h

[Out: Thu 12:00 → Thu 15:00 • 3h] — [Stay: 2d 20h] — [Back: Sun 11:20 → Sun 14:20 • 3h]

UASource: Aviasales (cached)

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

Est. USD 388

Updated ~0h agoExpires in ~2d

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ORD → ECP

2026-08-20 → 2026-08-25 • Direct • 3h

[Out: Thu 15:40 → Thu 18:40 • 3h] — [Stay: 5d] — [Back: Tue 18:54 → Tue 21:54 • 3h]

UASource: Aviasales (cached)

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

Est. USD 399

Updated ~12h agoExpires in ~1d

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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 06:00

Est. USD 406

Updated ~12h 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 06:00

Est. USD 427

Updated ~24h 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 06:00

Est. USD 436

Updated ~24h agoExpires in ~24h

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ORD → SAV

2026-08-02 → 2026-08-07 • Direct • 3h

[Out: Sun 12:00 → Sun 15:00 • 3h] — [Stay: 5d 1h] — [Back: Fri 15:30 → Fri 18:30 • 3h]

UASource: Aviasales (cached)

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

Est. USD 480

Updated ~24h agoExpires in ~24h

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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 06:00

Est. USD 540

Updated ~24h agoExpires in ~24h

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ORD → GUA

2026-08-21 → 2026-08-26 • Direct • 3h

[Out: Fri 20:40 → Fri 23:40 • 3h] — [Stay: 4d 15h] — [Back: Wed 14:20 → Wed 17:20 • 3h]

AVSource: Aviasales (cached)

See more dates for GUA• Inserted 2026-05-30 · Sat 06:00• Synced 2026-06-04 · Thu 06:00

Est. USD 545

Updated ~120h agoExpires in ~2d

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ORD → MTY

2026-06-19 → 2026-06-22 • Direct • 3h

[Out: Fri 06:30 → Fri 09:30 • 3h] — [Stay: 3d 15h] — [Back: Tue 24:35 → Tue 03:35 • 3h]

VBSource: Aviasales (cached)

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

Est. USD 581

Updated ~0h agoExpires in ~2d

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ORD → REK

2026-09-09 → 2026-09-16 • Direct • 3h

[Out: Thu 24:25 → Thu 03:25 • 3h] — [Stay: 6d 16h] — [Back: Wed 19:45 → Wed 22:45 • 3h]

FISource: Aviasales (cached)

See more dates for REK• Inserted 2026-05-25 · Mon 06:00• Synced 2026-06-04 · Thu 06:00

Est. USD 585

Updated ~240h agoExpires in ~2d

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ORD → Bogotá (BOG)

2026-06-09 → 2026-06-12 • Direct • 3h

[Out: Wed 04:20 → Wed 07:20 • 3h] — [Stay: 2d 13h] — [Back: Fri 19:50 → Fri 22:50 • 3h]

AVSource: Aviasales (cached)

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

Est. USD 696

Updated ~12h agoExpires in ~6h

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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 06:00

Est. USD 708

Updated ~24h agoExpires in ~24h

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ORD → Barcelona (BCN)

2026-07-24 → 2026-08-04 • Direct • 3h

[Out: Sat 02:40 → Sat 05:40 • 3h] — [Stay: 10d 8h] — [Back: Tue 13:15 → Tue 16:15 • 3h]

UASource: Aviasales (cached)

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

Est. USD 757

Updated ~24h agoExpires in ~24h

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ORD → Warsaw (WAW)

2026-08-12 → 2026-08-27 • Direct • 3h

[Out: Thu 02:50 → Thu 05:50 • 3h] — [Stay: 14d 4h] — [Back: Thu 10:00 → Thu 13:00 • 3h]

LOSource: Aviasales (cached)

See more dates for WAW• Inserted 2026-05-27 · Wed 18:00• Synced 2026-06-04 · Thu 06:00

Est. USD 820

Updated ~180h agoExpires in ~2d

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ORD → Rome (ROM)

2026-09-08 → 2026-09-15 • Direct • 3h

[Out: Tue 20:50 → Wed 01:50 • 3h] — [Stay: 6d 8h] — [Back: Tue 09:45 → Tue 10:45 • 3h]

UASource: Aviasales (cached)

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

Est. USD 823

Updated ~0h agoExpires in ~2d

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ORD → Panama City (PTY)

2026-07-12 → 2026-07-19 • Direct • 3h

[Out: Sun 06:20 → Sun 09:20 • 3h] — [Stay: 7d 4h] — [Back: Sun 13:10 → Sun 16:10 • 3h]

CMSource: Aviasales (cached)

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

Est. USD 833

Updated ~0h agoExpires in ~2d

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ORD → Copenhagen (CPH)

2026-08-05 → 2026-08-12 • Direct • 3h

[Out: Thu 24:15 → Thu 03:15 • 3h] — [Stay: 6d 9h] — [Back: Wed 11:55 → Wed 14:55 • 3h]

SKSource: Aviasales (cached)

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

Est. USD 836

Updated ~12h agoExpires in ~1d

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ORD → EDINBURGH AIRPORT (EDI)

2026-10-06 → 2026-10-12 • Direct • 3h

[Out: Tue 23:30 → Wed 02:30 • 3h] — [Stay: 5d 8h] — [Back: Mon 10:30 → Mon 13:30 • 3h]

UASource: Aviasales (cached)

See more dates for EDI• Inserted 2026-06-02 · Tue 18:00• Synced 2026-06-04 · Thu 06:00

Est. USD 879

Updated ~36h agoExpires in ~12h

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ORD → ISTANBUL AIRPORT (IST)

2026-11-10 → 2026-11-20 • Direct • 3h

[Out: Tue 17:45 → Tue 20:45 • 3h] — [Stay: 9d 8h] — [Back: Fri 04:35 → Fri 07:35 • 3h]

TKSource: Aviasales (cached)

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

Est. USD 912

Updated ~12h agoExpires in ~1d

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ORD → Milan (MIL)

2026-08-03 → 2026-08-17 • Direct • 3h

[Out: Tue 02:40 → Tue 05:40 • 3h] — [Stay: 13d 8h] — [Back: Mon 13:20 → Mon 16:20 • 3h]

UASource: Aviasales (cached)

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

Est. USD 1,013

Updated ~12h agoExpires in ~1d

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Price may differ at booking.

ORD → Athens (ATH)

2026-09-26 → 2026-10-22 • Direct • 3h

[Out: Sat 22:25 → Sun 01:25 • 3h] — [Stay: 25d 6h] — [Back: Thu 07:45 → Thu 10:45 • 3h]

AASource: Aviasales (cached)

See more dates for ATH• Inserted 2026-03-05 · Thu 18:00• Synced 2026-06-04 · Thu 06:00

Est. USD 1,031

Updated ~2172h agoExpires in ~2d

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ORD → Dubai (DXB)

2026-07-22 → 2026-08-19 • Direct • 3h

[Out: Thu 01:35 → Thu 04:35 • 3h] — [Stay: 27d 1h] — [Back: Wed 05:55 → Wed 08:55 • 3h]

EKSource: Aviasales (cached)

See more dates for DXB• Inserted 2026-06-02 · Tue 18:00• Synced 2026-06-04 · Thu 06:00

Est. USD 1,147

Updated ~36h agoExpires in ~12h

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Price may differ at booking.

ORD → CAPODICHINO AIRPORT (NAP)

2026-07-01 → 2026-07-31 • Direct • 3h

[Out: Wed 22:29 → Thu 01:29 • 3h] — [Stay: 29d 12h] — [Back: Fri 13:00 → Fri 16:00 • 3h]

Iberia (IB)Source: Aviasales (cached)

See more dates for NAP• Inserted 2026-06-02 · Tue 18:00• Synced 2026-06-04 · Thu 06:00

Est. USD 1,299

Updated ~36h agoExpires in ~12h

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ORD → Hong Kong (HKG)

2026-12-03 → 2026-12-10 • Direct • 3h

[Out: Thu 20:35 → Thu 23:35 • 3h] — [Stay: 6d 5h] — [Back: Thu 04:35 → Thu 07:35 • 3h]

CXSource: Aviasales (cached)

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

Est. USD 1,644

Updated ~24h agoExpires in ~24h

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ORD → PLS

2026-11-21 → 2026-11-28 • Direct • 3h

[Out: Sat 14:45 → Sat 17:45 • 3h] — [Stay: 7d 3h] — [Back: Sat 20:25 → Sat 23:25 • 3h]

UASource: Aviasales (cached)

See more dates for PLS• Inserted 2026-03-26 · Thu 18:00• Synced 2026-06-04 · Thu 06:00

Est. USD 1,824

Updated ~1668h agoExpires in ~2d

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Deal may be stale — use “View deal” to verify.