Flights from Chicago Midway

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

Last synced: Mon 19:00

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SortPrice Freshness ScoreViewBest per destination All dates

SourceAll Amadeus Aviasales

StopsDirect 1 stop 2+ stops All

AirlineAll WN

Showing 13 destinations • From 21 matching deals

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 2026-07-20 · Mon 19:00

Est. USD 200

Updated ~13h agoExpires in ~1d

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MDW → Houston (HOU)

2026-08-19 → 2026-08-23 • Direct • 2h 25m

[Out: Thu 01:25 → Thu 03:50 • 2h 25m] — [Stay: 3d 7h] — [Back: Sun 10:40 → Sun 13:05 • 2h 25m]

Source: Aviasales (cached)

See more dates for HOU• Inserted 2026-07-19 · Sun 01:00• Cached since 2026-07-19 · Sun 24:15• Synced 2026-07-20 · Mon 19:00

Est. USD 210

Cached ~42h agoExpires in ~0h

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MDW → Nashville (BNA)

2026-09-04 → 2026-09-06 • Direct • 1h 30m

[Out: Fri 22:30 → Sat 24:00 • 1h 30m] — [Stay: 1d 11h] — [Back: Sun 11:10 → Sun 12:40 • 1h 30m]

Source: Aviasales (cached)

See more dates for BNA• Inserted 2026-07-20 · Mon 01:00• Cached since 2026-07-19 · Sun 22:55• Synced 2026-07-20 · Mon 19:00

Est. USD 218

Cached ~18h agoExpires in ~1d

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MDW → OMA

2026-08-27 → 2026-09-03 • Direct • 3h

[Out: Thu 19:45 → Thu 22:45 • 3h] — [Stay: 6d 12h] — [Back: Thu 10:35 → Thu 13:35 • 3h]

WNSource: Aviasales (cached)

See more dates for OMA• Inserted 2026-07-19 · Sun 06:00• Synced 2026-07-20 · Mon 19:00

Est. USD 218

Updated ~37h agoExpires in ~5h

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MDW → Los Angeles (LAX)

2026-09-12 → 2026-09-19 • Direct • 3h

[Out: Sat 19:50 → Sat 22:50 • 3h] — [Stay: 7d 8h] — [Back: Sun 06:55 → Sun 09:55 • 3h]

WNSource: Aviasales (cached)

See more dates for LAX• Inserted 2026-07-19 · Sun 06:00• Synced 2026-07-20 · Mon 19:00

Est. USD 244

Updated ~37h agoExpires in ~5h

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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 2026-07-20 · Mon 19:00

Est. USD 245

Updated ~13h agoExpires in ~1d

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MDW → Baltimore (BWI)

2026-08-29 → 2026-08-30 • Direct • 3h

[Out: Sat 10:55 → Sat 13:55 • 3h] — [Stay: 1d 3h] — [Back: Sun 16:50 → Sun 19:50 • 3h]

WNSource: Aviasales (cached)

See more dates for BWI• Inserted 2026-07-19 · Sun 06:00• Synced 2026-07-20 · Mon 19:00

Est. USD 263

Updated ~37h agoExpires in ~5h

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MDW → Indianapolis (IND)

2026-08-20 → 2026-08-21 • Direct • 1h

[Out: Thu 15:10 → Thu 16:10 • 1h] — [Stay: 19h] — [Back: Fri 10:45 → Fri 11:45 • 1h]

Source: Aviasales (cached)

See more dates for IND• Inserted 2026-07-20 · Mon 19:00• Cached since 2026-07-20 · Mon 16:16• Synced 2026-07-20 · Mon 19:00

Est. USD 289

Cached ~0h 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 2026-07-20 · Mon 19:00

Est. USD 309

Updated ~13h agoExpires in ~1d

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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 2026-07-20 · Mon 19:00

Est. USD 329

Updated ~13h agoExpires in ~1d

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MDW → Pittsburgh (PIT)

2026-08-06 → 2026-08-09 • Direct • 1h 25m

[Out: Fri 24:40 → Fri 02:05 • 1h 25m] — [Stay: 2d 21h] — [Back: Sun 22:50 → Mon 24:15 • 1h 25m]

Source: Aviasales (cached)

See more dates for PIT• Inserted 2026-07-19 · Sun 01:00• Cached since 2026-07-18 · Sat 22:14• Synced 2026-07-20 · Mon 19:00

Est. USD 484

Cached ~42h agoExpires in ~0h

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MDW → PVD

2026-08-05 → 2026-08-10 • Direct • 3h

[Out: Wed 18:10 → Wed 21:10 • 3h] — [Stay: 5d 1h] — [Back: Mon 22:10 → Tue 01:10 • 3h]

WNSource: Aviasales (cached)

See more dates for PVD• Inserted 2026-07-19 · Sun 06:00• Synced 2026-07-20 · Mon 19:00

Est. USD 550

Updated ~37h agoExpires in ~5h

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MDW → SRQ

2026-08-01 → 2026-08-08 • Direct • 2h 40m

[Out: Sat 14:25 → Sat 17:05 • 2h 40m] — [Stay: 7d 2h] — [Back: Sat 19:20 → Sat 22:00 • 2h 40m]

Source: Aviasales (cached)

See more dates for SRQ• Inserted 2026-07-19 · Sun 19:00• Cached since 2026-07-19 · Sun 18:08• Synced 2026-07-20 · Mon 19:00

Est. USD 660

Cached ~24h agoExpires in ~18h

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