Flights from Chicago Midway

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

Last synced: Tue 07:00

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SortPrice Freshness ScoreViewBest per destination All dates

SourceAll Amadeus Aviasales

StopsDirect 1 stop 2+ stops All

AirlineAll G4 WN Y4

Showing 14 destinations • Airline filter: WN • From 15 matching deals (out of 27 total deals)

MDW → Cincinnati (CVG)

2026-08-27 → 2026-08-31 • Direct • 3h

[Out: Thu 23:10 → Fri 02:10 • 3h] — [Stay: 3d 10h] — [Back: Mon 12:10 → Mon 15:10 • 3h]

WNSource: Aviasales (cached)

See more dates for CVG• Inserted 2026-07-21 · Tue 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 157

Updated ~1h agoExpires in ~2d

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MDW → New York (NYC)

2026-07-25 → 2026-07-27 • Direct • 3h

[Out: Sat 10:00 → Sat 13:00 • 3h] — [Stay: 1d 21h] — [Back: Mon 10:00 → Mon 13:00 • 3h]

WNSource: Aviasales (cached)

See more dates for NYC• Inserted 2026-07-21 · Tue 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 183

Updated ~1h agoExpires in ~14h

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MDW → Denver (DEN)

2026-08-01 → 2026-08-03 • Direct • 3h

[Out: Sat 10:25 → Sat 13:25 • 3h] — [Stay: 2d 10h] — [Back: Mon 23:35 → Tue 02:35 • 3h]

WNSource: Aviasales (cached)

See more dates for DEN• Inserted 2026-07-20 · Mon 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 200

Updated ~25h agoExpires in ~20h

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MDW → Nashville (BNA)

2026-09-04 → 2026-09-06 • Direct • 3h

[Out: Fri 22:30 → Sat 01:30 • 3h] — [Stay: 1d 10h] — [Back: Sun 11:10 → Sun 14:10 • 3h]

WNSource: Aviasales (cached)

See more dates for BNA• Inserted 2026-07-20 · Mon 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 218

Updated ~25h agoExpires in ~20h

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MDW → Seattle (SEA)

2026-08-13 → 2026-08-16 • Direct • 3h

[Out: Fri 02:20 → Fri 05:20 • 3h] — [Stay: 2d 7h] — [Back: Sun 12:40 → Sun 15:40 • 3h]

WNSource: Aviasales (cached)

See more dates for SEA• Inserted 2026-07-20 · Mon 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 245

Updated ~25h agoExpires in ~20h

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MDW → Baltimore (BWI)

2026-08-20 → 2026-08-24 • Direct • 3h

[Out: Thu 12:30 → Thu 15:30 • 3h] — [Stay: 4d 7h] — [Back: Mon 22:40 → Tue 01:40 • 3h]

WNSource: Aviasales (cached)

See more dates for BWI• Inserted 2026-07-20 · Mon 18:00• Synced 2026-07-21 · Tue 07:00

Est. USD 266

Updated ~13h agoExpires in ~1d

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MDW → SRQ

2026-09-19 → 2026-09-26 • Direct • 3h

[Out: Sat 12:50 → Sat 15:50 • 3h] — [Stay: 7d 4h] — [Back: Sat 19:20 → Sat 22:20 • 3h]

WNSource: Aviasales (cached)

See more dates for SRQ• Inserted 2026-07-21 · Tue 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 282

Updated ~1h agoExpires in ~2d

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MDW → Indianapolis (IND)

2026-08-20 → 2026-08-21 • Direct • 3h

[Out: Thu 15:10 → Thu 18:10 • 3h] — [Stay: 17h] — [Back: Fri 10:45 → Fri 13:45 • 3h]

WNSource: Aviasales (cached)

See more dates for IND• Inserted 2026-07-20 · Mon 18:00• Synced 2026-07-21 · Tue 07:00

Est. USD 289

Updated ~13h agoExpires in ~1d

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MDW → Philadelphia (PHL)

2026-11-21 → 2026-11-24 • Direct • 3h

[Out: Sun 24:55 → Sun 03:55 • 3h] — [Stay: 2d 13h] — [Back: Tue 17:10 → Tue 20:10 • 3h]

WNSource: Aviasales (cached)

See more dates for PHL• Inserted 2026-07-21 · Tue 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 296

Updated ~1h agoExpires in ~2d

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MDW → FMY

2026-09-16 → 2026-09-30 • Direct • 3h

[Out: Wed 23:00 → Thu 02:00 • 3h] — [Stay: 13d 9h] — [Back: Wed 11:10 → Wed 14:10 • 3h]

WNSource: Aviasales (cached)

See more dates for FMY• Inserted 2026-07-20 · Mon 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 309

Updated ~25h agoExpires in ~20h

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MDW → LGB

2026-08-15 → 2026-08-17 • Direct • 3h

[Out: Sat 18:50 → Sat 21:50 • 3h] — [Stay: 2d 9h] — [Back: Tue 06:55 → Tue 09:55 • 3h]

WNSource: Aviasales (cached)

See more dates for LGB• Inserted 2026-07-21 · Tue 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 312

Updated ~1h agoExpires in ~2d

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MDW → Charlotte (CLT)

2026-09-01 → 2026-09-15 • Direct • 3h

[Out: Tue 23:10 → Wed 02:10 • 3h] — [Stay: 13d 20h] — [Back: Tue 22:35 → Wed 01:35 • 3h]

WNSource: Aviasales (cached)

See more dates for CLT• Inserted 2026-07-20 · Mon 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 329

Updated ~25h agoExpires in ~20h

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MDW → Pittsburgh (PIT)

2026-08-07 → 2026-08-09 • Direct • 3h

[Out: Sat 24:40 → Sat 03:40 • 3h] — [Stay: 1d 19h] — [Back: Sun 22:50 → Mon 01:50 • 3h]

WNSource: Aviasales (cached)

See more dates for PIT• Inserted 2026-07-19 · Sun 18:00• Synced 2026-07-21 · Tue 07:00

Est. USD 484

Updated ~37h agoExpires in ~8h

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MDW → ROC

2026-07-27 → 2026-07-28 • Direct • 3h

[Out: Mon 18:20 → Mon 21:20 • 3h] — [Stay: 1d 2h] — [Back: Tue 23:05 → Wed 02:05 • 3h]

WNSource: Aviasales (cached)

See more dates for ROC• Inserted 2026-07-21 · Tue 06:00• Synced 2026-07-21 · Tue 07:00

Est. USD 629

Updated ~1h agoExpires in ~14h

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Price may differ at booking.