Flights from Chicago Midway

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

Last synced: Sat 03:30

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AirlineAll F9 WN Y4

Showing 2 destinations • Airline filter: Y4 • From 2 matching deals (out of 29 total deals)

MDW → Guadalajara (GDL)

2026-07-21 → 2026-07-29 • Direct • 3h

[Out: Wed 01:49 → Wed 04:49 • 3h] — [Stay: 7d 14h] — [Back: Wed 19:01 → Wed 22:01 • 3h]

Y4Source: Aviasales (cached)

See more dates for GDL• Inserted 2026-06-04 · Thu 06:00• Synced 2026-06-06 · Sat 03:30

Est. USD 349

Updated ~46h agoExpires in ~0h

Price may differ at booking.

MDW → BJX

2026-06-25 → 2026-07-18 • Direct • 3h

[Out: Thu 20:29 → Thu 23:29 • 3h] — [Stay: 22d 15h] — [Back: Sat 14:09 → Sat 17:09 • 3h]

Y4Source: Aviasales (cached)

See more dates for BJX• Inserted 2026-06-05 · Fri 06:00• Synced 2026-06-06 · Sat 03:30

Est. USD 408

Updated ~22h agoExpires in ~1d

Price may differ at booking.