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 F9 WN Y4

Showing 22 destinations • From 30 matching deals

MDW → TUL

2026-10-05 → 2026-10-12 • Direct • 3h

[Out: Tue 02:25 → Tue 05:25 • 3h] — [Stay: 6d 16h] — [Back: Mon 20:55 → Mon 23:55 • 3h]

WNSource: Aviasales (cached)

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

Est. USD 148

Updated ~9h agoExpires in ~2d

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MDW → Las Vegas (LAS)

2026-08-21 → 2026-08-23 • Direct • 3h

[Out: Fri 11:40 → Fri 14:40 • 3h] — [Stay: 1d 17h] — [Back: Sun 07:20 → Sun 10:20 • 3h]

WNSource: Aviasales (cached)

See more dates for LAS• Inserted 2026-06-29 · Mon 06:00• Synced 2026-06-30 · Tue 15:30

Est. USD 149

Updated ~34h agoExpires in ~12h

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MDW → EDWARD L LOGAN INTL (BOS)

2026-08-16 → 2026-08-23 • Direct • 2h 25m

[Out: Sun 11:00 → Sun 13:25 • 2h 25m] — [Stay: 7d 12h] — [Back: Mon 01:05 → Mon 03:30 • 2h 25m]

Source: Aviasales (cached)

See more dates for BOS• Inserted 2026-06-29 · Mon 01:00• Cached since 2026-06-28 · Sun 18:56• Synced 2026-06-30 · Tue 15:30

Est. USD 159

Cached ~38h agoExpires in ~7h

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MDW → Cleveland (CLE)

2026-08-05 → 2026-08-06 • Direct • 1h 17m

[Out: Wed 13:35 → Wed 14:52 • 1h 17m] — [Stay: 22h] — [Back: Thu 12:50 → Thu 14:08 • 1h 18m]

Source: Aviasales (cached)

See more dates for CLE• Inserted 2026-06-30 · Tue 01:00• Cached since 2026-06-29 · Mon 22:27• Synced 2026-06-30 · Tue 15:30

Est. USD 165

Cached ~14h agoExpires in ~1d

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MDW → New York (NYC)

2026-08-11 → 2026-08-13 • Direct • 2h 7m

[Out: Tue 10:10 → Tue 12:17 • 2h 7m] — [Stay: 1d 22h] — [Back: Thu 10:00 → Thu 12:08 • 2h 8m]

Source: Aviasales (cached)

See more dates for NYC• Inserted 2026-06-30 · Tue 01:00• Cached since 2026-06-28 · Sun 20:08• Synced 2026-06-30 · Tue 15:30

Est. USD 182

Cached ~14h agoExpires in ~1d

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MDW → Fort Lauderdale (FLL)

2026-09-11 → 2026-09-15 • Direct • 2h 57m

[Out: Fri 12:40 → Fri 15:37 • 2h 57m] — [Stay: 3d 20h] — [Back: Tue 11:20 → Tue 14:18 • 2h 58m]

Source: Aviasales (cached)

See more dates for FLL• Inserted 2026-06-29 · Mon 01:00• Cached since 2026-06-28 · Sun 23:37• Synced 2026-06-30 · Tue 15:30

Est. USD 200

Cached ~38h agoExpires in ~7h

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MDW → JAX

2026-07-28 → 2026-07-29 • Direct • 2h 25m

[Out: Tue 23:20 → Wed 01:45 • 2h 25m] — [Stay: 21h] — [Back: Wed 22:50 → Thu 01:15 • 2h 25m]

Source: Aviasales (cached)

See more dates for JAX• Inserted 2026-06-29 · Mon 01:00• Cached since 2026-06-28 · Sun 20:46• Synced 2026-06-30 · Tue 15:30

Est. USD 219

Cached ~38h agoExpires in ~7h

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MDW → Dallas (DFW)

2026-07-07 → 2026-07-14 • Direct • 3h

[Out: Tue 22:46 → Wed 01:46 • 3h] — [Stay: 6d 19h] — [Back: Tue 21:13 → Wed 24:13 • 3h]

F9Source: Aviasales (cached)

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

Est. USD 224

Updated ~9h agoExpires in ~6h

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MDW → Tampa (TPA)

2026-08-06 → 2026-08-10 • Direct • 2h 35m

[Out: Fri 24:55 → Fri 03:30 • 2h 35m] — [Stay: 3d 6h] — [Back: Mon 09:15 → Mon 11:50 • 2h 35m]

Source: Aviasales (cached)

See more dates for TPA• Inserted 2026-06-29 · Mon 01:00• Cached since 2026-06-28 · Sun 15:50• Synced 2026-06-30 · Tue 15:30

Est. USD 236

Cached ~38h agoExpires in ~7h

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MDW → ORF

2026-07-27 → 2026-07-30 • Direct • 3h

[Out: Tue 24:00 → Tue 03:00 • 3h] — [Stay: 2d 20h] — [Back: Thu 23:15 → Fri 02:15 • 3h]

WNSource: Aviasales (cached)

See more dates for ORF• Inserted 2026-06-28 · Sun 18:00• Synced 2026-06-30 · Tue 15:30

Est. USD 272

Updated ~45h agoExpires in ~0h

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MDW → DTT

2026-08-15 → 2026-08-16 • Direct • 3h

[Out: Sat 20:35 → Sat 23:35 • 3h] — [Stay: 1d] — [Back: Sun 23:30 → Mon 02:30 • 3h]

WNSource: Aviasales (cached)

See more dates for DTT• Inserted 2026-06-29 · Mon 06:00• Synced 2026-06-30 · Tue 15:30

Est. USD 285

Updated ~34h agoExpires in ~1d

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MDW → Washington (WAS)

2026-07-14 → 2026-07-15 • Direct • 3h

[Out: Tue 13:30 → Tue 16:30 • 3h] — [Stay: 1d] — [Back: Wed 16:00 → Wed 19:00 • 3h]

WNSource: Aviasales (cached)

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

Est. USD 307

Updated ~9h agoExpires in ~2d

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MDW → Nashville (BNA)

2026-07-21 → 2026-07-24 • Direct • 1h 32m

[Out: Tue 13:40 → Tue 15:12 • 1h 32m] — [Stay: 3d 10h] — [Back: Sat 01:25 → Sat 02:58 • 1h 33m]

Source: Aviasales (cached)

See more dates for BNA• Inserted 2026-06-30 · Tue 13:00• Cached since 2026-06-28 · Sun 18:08• Synced 2026-06-30 · Tue 15:30

Est. USD 309

Cached ~2h agoExpires in ~2d

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MDW → San Diego (SAN)

2026-07-30 → 2026-08-04 • Direct • 3h

[Out: Fri 02:10 → Fri 05:10 • 3h] — [Stay: 5d 1h] — [Back: Wed 05:40 → Wed 08:40 • 3h]

WNSource: Aviasales (cached)

See more dates for SAN• Inserted 2026-06-28 · Sun 18:00• Synced 2026-06-30 · Tue 15:30

Est. USD 339

Updated ~45h agoExpires in ~0h

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MDW → San Francisco (SFO)

2026-08-28 → 2026-09-01 • Direct • 3h

[Out: Fri 15:15 → Fri 18:15 • 3h] — [Stay: 4d 12h] — [Back: Wed 06:40 → Wed 09:40 • 3h]

WNSource: Aviasales (cached)

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

Est. USD 354

Updated ~9h agoExpires in ~2d

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MDW → San Jose (SJC)

2026-07-24 → 2026-07-28 • Direct • 3h

[Out: Sat 01:50 → Sat 04:50 • 3h] — [Stay: 4d 1h] — [Back: Wed 05:55 → Wed 08:55 • 3h]

WNSource: Aviasales (cached)

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

Est. USD 384

Updated ~9h agoExpires in ~2d

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MDW → Salt Lake City (SLC)

2026-10-17 → 2026-10-23 • Direct • 3h

[Out: Sat 19:45 → Sat 22:45 • 3h] — [Stay: 5d 15h] — [Back: Fri 14:00 → Fri 17:00 • 3h]

WNSource: Aviasales (cached)

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

Est. USD 438

Updated ~9h agoExpires in ~2d

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MDW → Raleigh (RDU)

2026-07-04 → 2026-07-05 • Direct • 3h

[Out: Sat 20:45 → Sat 23:45 • 3h] — [Stay: 12h] — [Back: Sun 11:15 → Sun 14:15 • 3h]

WNSource: Aviasales (cached)

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

Est. USD 493

Updated ~9h agoExpires in ~6h

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MDW → ROC

2026-07-09 → 2026-07-13 • Direct • 1h 45m

[Out: Thu 23:50 → Fri 01:35 • 1h 45m] — [Stay: 3d 22h] — [Back: Mon 23:35 → Tue 01:20 • 1h 45m]

Source: Aviasales (cached)

See more dates for ROC• Inserted 2026-06-30 · Tue 01:00• Cached since 2026-06-29 · Mon 23:02• Synced 2026-06-30 · Tue 15:30

Est. USD 501

Cached ~14h agoExpires in ~1d

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MDW → COS

2026-07-23 → 2026-07-30 • Direct • 3h

[Out: Thu 17:30 → Thu 20:30 • 3h] — [Stay: 7d] — [Back: Thu 20:40 → Thu 23:40 • 3h]

WNSource: Aviasales (cached)

See more dates for COS• Inserted 2026-06-29 · Mon 18:00• Synced 2026-06-30 · Tue 15:30

Est. USD 502

Updated ~22h agoExpires in ~1d

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MDW → Cancún (CUN)

2026-10-13 → 2026-10-20 • Direct • 3h

[Out: Tue 14:05 → Tue 17:05 • 3h] — [Stay: 7d 3h] — [Back: Tue 19:45 → Tue 22:45 • 3h]

WNSource: Aviasales (cached)

See more dates for CUN• Inserted 2026-06-28 · Sun 18:00• Synced 2026-06-30 · Tue 15:30

Est. USD 546

Updated ~45h agoExpires in ~0h

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MDW → BJX

2026-07-21 → 2026-07-28 • Direct • 3h

[Out: Tue 20:29 → Tue 23:29 • 3h] — [Stay: 6d 15h] — [Back: Tue 14:09 → Tue 17:09 • 3h]

Y4Source: Aviasales (cached)

See more dates for BJX• Inserted 2026-06-28 · Sun 18:00• Synced 2026-06-30 · Tue 15:30

Est. USD 688

Updated ~45h agoExpires in ~0h

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