Flights MDW → OAK

Curated weekend trips for the next few weeks. Prices are estimates until you verify.

Outbound partner clickouts are enabled only for deals updated in the last 72h.

ToolsBest dates calendar Date grid Direct flights Dates → destinations Under CHF 100

Quick summary

Looking for a quick escape? This route is currently showing direct options. Typical outbound flight time is about 3h. Common windows are ~3 nights. Best current pick is around USD 296.

More deals from MDW Origin stats Best month to go Under CHF 100

2026-07-16 → 2026-07-19

Direct • 3h

[Out: Fri 02:40 → Fri 05:40 • 3h] — [Stay: 3d 1h] — [Back: Mon 06:40 → Mon 09:40 • 3h]

Source: Aviasales (cached) • Inserted 2026-06-06 · Sat 06:00 • Synced 2026-06-06 · Sat 07:00

Est. USD 296

Updated ~1h agoExpires in ~2d

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Price may differ at booking.

2026-07-16 → 2026-07-19

Direct • 4h 25m

[Out: Fri 02:40 → Fri 07:05 • 4h 25m] — [Stay: 3d] — [Back: Mon 06:40 → Mon 11:05 • 4h 25m]

Source: Aviasales (cached) • Inserted 2026-06-06 · Sat 07:00 • Cached since 2026-06-06 · Sat 04:11 • Synced 2026-06-06 · Sat 07:00

Est. USD 296

Cached ~0h agoExpires in ~2d

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Price may differ at booking.

2026-07-04 → 2026-07-17

Direct • 5h 52m

[Out: Sat 15:20 → Sat 21:12 • 5h 52m] — [Stay: 13d 9h] — [Back: Sat 06:40 → Sat 12:33 • 5h 53m]

Source: Aviasales (cached) • Inserted 2026-06-06 · Sat 01:00 • Cached since 2026-05-31 · Sun 10:46 • Synced 2026-06-06 · Sat 07:00

Est. USD 387

Cached ~6h agoExpires in ~17h

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Price may differ at booking.

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