Flights from Chicago Midway

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

Last synced: Tue 15:30

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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 27 deals • Stops: All

MDW → Cincinnati (CVG)

2026-08-27 → 2026-08-31 • Direct • 1h 10m

[Out: Thu 23:10 → Fri 24:20 • 1h 10m] — [Stay: 3d 12h] — [Back: Mon 12:10 → Mon 13:20 • 1h 10m]

Source: Aviasales (cached)

See more dates for CVG• Inserted 2026-07-21 · Tue 01:00• Cached since 2026-07-21 · Tue 01:20• Synced 2026-07-21 · Tue 15:30

Est. USD 157

Cached ~15h agoExpires in ~1d

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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 15:30

Est. USD 157

Updated ~10h 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 15:30

Est. USD 183

Updated ~10h agoExpires in ~7h

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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 15:30

Est. USD 200

Updated ~33h agoExpires in ~13h

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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 2026-07-21 · Tue 15:30

Est. USD 218

Cached ~39h agoExpires in ~8h

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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 15:30

Est. USD 218

Updated ~33h agoExpires in ~13h

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MDW → VPS

2026-07-31 → 2026-08-03 • Direct • 2h 17m

[Out: Sat 02:21 → Sat 04:38 • 2h 17m] — [Stay: 2d 19h] — [Back: Mon 23:10 → Tue 01:27 • 2h 17m]

Source: Aviasales (cached)

See more dates for VPS• Inserted 2026-07-21 · Tue 01:00• Cached since 2026-07-20 · Mon 19:25• Synced 2026-07-21 · Tue 15:30

Est. USD 238

Cached ~15h agoExpires in ~1d

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MDW → VPS

2026-07-31 → 2026-08-03 • Direct • 3h

[Out: Sat 02:21 → Sat 05:21 • 3h] — [Stay: 2d 18h] — [Back: Mon 23:10 → Tue 02:10 • 3h]

G4Source: Aviasales (cached)

See more dates for VPS• Inserted 2026-07-21 · Tue 06:00• Synced 2026-07-21 · Tue 15:30

Est. USD 238

Updated ~10h agoExpires in ~2d

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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 15:30

Est. USD 245

Updated ~33h agoExpires in ~13h

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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 15:30

Est. USD 266

Updated ~22h 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 15:30

Est. USD 282

Updated ~10h agoExpires in ~2d

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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 2026-07-21 · Tue 15:30

Est. USD 289

Cached ~20h agoExpires in ~1d

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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 15:30

Est. USD 289

Updated ~22h 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 15:30

Est. USD 296

Updated ~10h 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 15:30

Est. USD 309

Updated ~33h agoExpires in ~13h

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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 15:30

Est. USD 312

Updated ~10h agoExpires in ~2d

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MDW → LGB

2026-08-15 → 2026-08-17 • Direct • 4h 2m

[Out: Sat 18:50 → Sat 22:52 • 4h 2m] — [Stay: 2d 8h] — [Back: Tue 06:55 → Tue 10:58 • 4h 3m]

Source: Aviasales (cached)

See more dates for LGB• Inserted 2026-07-21 · Tue 07:00• Cached since 2026-07-21 · Tue 01:53• Synced 2026-07-21 · Tue 15:30

Est. USD 312

Cached ~9h agoExpires in ~2d

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MDW → LGB

2026-09-12 → 2026-09-19 • Direct • 4h 7m

[Out: Sat 18:50 → Sat 22:57 • 4h 7m] — [Stay: 7d 8h] — [Back: Sun 06:55 → Sun 11:03 • 4h 8m]

Source: Aviasales (cached)

See more dates for LGB• Inserted 2026-07-21 · Tue 01:00• Cached since 2026-07-19 · Sun 03:50• Synced 2026-07-21 · Tue 15:30

Est. USD 316

Cached ~15h 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 2026-07-21 · Tue 15:30

Est. USD 329

Updated ~33h agoExpires in ~13h

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MDW → MLM

2026-07-31 → 2026-08-02 • Direct • 3h

[Out: Fri 19:32 → Fri 22:32 • 3h] — [Stay: 1d 15h] — [Back: Sun 13:14 → Sun 16:14 • 3h]

Y4Source: Aviasales (cached)

See more dates for MLM• Inserted 2026-07-21 · Tue 06:00• Synced 2026-07-21 · Tue 15:30

Est. USD 414

Updated ~10h agoExpires in ~2d

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MDW → MLM

2026-07-31 → 2026-08-02 • Direct • 4h

[Out: Fri 19:32 → Fri 23:32 • 4h] — [Stay: 1d 14h] — [Back: Sun 13:14 → Sun 17:14 • 4h]

Source: Aviasales (cached)

See more dates for MLM• Inserted 2026-07-21 · Tue 01:00• Cached since 2026-07-20 · Mon 18:06• Synced 2026-07-21 · Tue 15:30

Est. USD 414

Cached ~15h agoExpires in ~1d

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MDW → Pittsburgh (PIT)

2026-08-07 → 2026-08-09 • Direct • 1h 25m

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

Source: Aviasales (cached)

See more dates for PIT• Inserted 2026-07-19 · Sun 19:00• Cached since 2026-07-18 · Sat 22:13• Synced 2026-07-21 · Tue 15:30

Est. USD 484

Cached ~45h agoExpires in ~2h

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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 15:30

Est. USD 484

Updated ~46h agoExpires in ~1h

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MDW → ROC

2026-07-27 → 2026-07-28 • Direct • 1h 40m

[Out: Mon 18:20 → Mon 20:00 • 1h 40m] — [Stay: 1d 3h] — [Back: Tue 23:05 → Wed 24:45 • 1h 40m]

Source: Aviasales (cached)

See more dates for ROC• Inserted 2026-07-21 · Tue 01:00• Cached since 2026-07-20 · Mon 21:39• Synced 2026-07-21 · Tue 15:30

Est. USD 629

Cached ~15h agoExpires in ~2h

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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 15:30

Est. USD 629

Updated ~10h agoExpires in ~7h

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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 2026-07-21 · Tue 15:30

Est. USD 660

Cached ~45h agoExpires in ~2h

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MDW → SRQ

2026-08-01 → 2026-08-08 • Direct • 3h

[Out: Sat 14:25 → Sat 17:25 • 3h] — [Stay: 7d 2h] — [Back: Sat 19:20 → Sat 22:20 • 3h]

WNSource: Aviasales (cached)

See more dates for SRQ• Inserted 2026-07-20 · Mon 06:00• Synced 2026-07-21 · Tue 15:30

Est. USD 660

Updated ~33h agoExpires in ~13h

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