Flights from Chicago Midway

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

Last synced: Sat 07:00

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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 38 deals • Stops: All

MDW → New York (NYC)

2026-07-31 → 2026-08-03 • Direct • 2h 12m

[Out: Fri 10:15 → Fri 12:27 • 2h 12m] — [Stay: 2d 23h] — [Back: Mon 11:25 → Mon 13:38 • 2h 13m]

Source: Aviasales (cached)

See more dates for NYC• Inserted 2026-06-04 · Thu 19:00• Cached since 2026-06-04 · Thu 17:38• Synced 2026-06-06 · Sat 07:00

Est. USD 124

Cached ~36h agoExpires in ~12h

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MDW → New York (NYC)

2026-07-31 → 2026-08-03 • Direct • 3h

[Out: Fri 10:15 → Fri 13:15 • 3h] — [Stay: 2d 22h] — [Back: Mon 11:25 → Mon 14:25 • 3h]

WNSource: Aviasales (cached)

See more dates for NYC• Inserted 2026-06-04 · Thu 18:00• Synced 2026-06-06 · Sat 07:00

Est. USD 124

Updated ~37h agoExpires in ~11h

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MDW → Tampa (TPA)

2026-07-21 → 2026-07-25 • Direct • 3h

[Out: Wed 01:15 → Wed 04:15 • 3h] — [Stay: 3d 5h] — [Back: Sat 09:30 → Sat 12:30 • 3h]

WNSource: Aviasales (cached)

See more dates for TPA• Inserted 2026-06-04 · Thu 18:00• Synced 2026-06-06 · Sat 07:00

Est. USD 134

Updated ~37h agoExpires in ~23h

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MDW → EDWARD L LOGAN INTL (BOS)

2026-07-05 → 2026-07-07 • Direct • 3h

[Out: Sun 10:15 → Sun 13:15 • 3h] — [Stay: 1d 20h] — [Back: Tue 09:35 → Tue 12:35 • 3h]

WNSource: Aviasales (cached)

See more dates for BOS• Inserted 2026-06-05 · Fri 18:00• Synced 2026-06-06 · Sat 07:00

Est. USD 194

Updated ~13h agoExpires in ~1d

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MDW → Houston (HOU)

2026-07-04 → 2026-07-08 • Direct • 2h 32m

[Out: Sat 11:50 → Sat 14:22 • 2h 32m] — [Stay: 4d 12h] — [Back: Thu 02:25 → Thu 04:58 • 2h 33m]

Source: Aviasales (cached)

See more dates for HOU• Inserted 2026-06-05 · Fri 19:00• Cached since 2026-06-05 · Fri 15:17• Synced 2026-06-06 · Sat 07:00

Est. USD 232

Cached ~12h agoExpires in ~1d

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MDW → Houston (HOU)

2026-07-04 → 2026-07-08 • Direct • 3h

[Out: Sat 11:50 → Sat 14:50 • 3h] — [Stay: 4d 12h] — [Back: Thu 02:25 → Thu 05:25 • 3h]

WNSource: Aviasales (cached)

See more dates for HOU• Inserted 2026-06-05 · Fri 18:00• Synced 2026-06-06 · Sat 07:00

Est. USD 232

Updated ~13h agoExpires in ~1d

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MDW → Washington (WAS)

2026-07-07 → 2026-07-09 • Direct • 1h 55m

[Out: Tue 10:40 → Tue 12:35 • 1h 55m] — [Stay: 2d 12h] — [Back: Fri 01:00 → Fri 02:55 • 1h 55m]

Source: Aviasales (cached)

See more dates for WAS• Inserted 2026-06-06 · Sat 07:00• Cached since 2026-06-04 · Thu 04:43• Synced 2026-06-06 · Sat 07:00

Est. USD 236

Cached ~0h agoExpires in ~24h

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MDW → Washington (WAS)

2026-07-07 → 2026-07-09 • Direct • 3h

[Out: Tue 10:40 → Tue 13:40 • 3h] — [Stay: 2d 11h] — [Back: Fri 01:00 → Fri 04:00 • 3h]

WNSource: Aviasales (cached)

See more dates for WAS• Inserted 2026-06-06 · Sat 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 236

Updated ~1h agoExpires in ~2d

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MDW → MYR

2026-07-07 → 2026-07-08 • Direct • 2h 5m

[Out: Tue 23:45 → Wed 01:50 • 2h 5m] — [Stay: 10h] — [Back: Wed 11:55 → Wed 14:00 • 2h 5m]

Source: Aviasales (cached)

See more dates for MYR• Inserted 2026-06-04 · Thu 19:00• Cached since 2026-06-04 · Thu 14:58• Synced 2026-06-06 · Sat 07:00

Est. USD 239

Cached ~36h agoExpires in ~12h

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MDW → MYR

2026-07-07 → 2026-07-08 • Direct • 3h

[Out: Tue 23:45 → Wed 02:45 • 3h] — [Stay: 9h] — [Back: Wed 11:55 → Wed 14:55 • 3h]

WNSource: Aviasales (cached)

See more dates for MYR• Inserted 2026-06-04 · Thu 18:00• Synced 2026-06-06 · Sat 07:00

Est. USD 239

Updated ~37h agoExpires in ~11h

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MDW → Denver (DEN)

2026-07-23 → 2026-07-27 • Direct • 2h 30m

[Out: Thu 10:15 → Thu 12:45 • 2h 30m] — [Stay: 4d 14h] — [Back: Tue 02:50 → Tue 05:20 • 2h 30m]

Source: Aviasales (cached)

See more dates for DEN• Inserted 2026-05-26 · Tue 07:00• Cached since 2026-06-06 · Sat 24:55• Synced 2026-06-06 · Sat 07:00

Est. USD 250

Cached ~264h agoExpires in ~2d

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MDW → Houston (HOU)

2026-08-19 → 2026-08-23 • Direct • 3h

[Out: Thu 01:25 → Thu 04:25 • 3h] — [Stay: 3d 22h] — [Back: Mon 02:50 → Mon 05:50 • 3h]

WNSource: Aviasales (cached)

See more dates for HOU• Inserted 2026-06-05 · Fri 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 258

Updated ~25h agoExpires in ~23h

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MDW → San Francisco (SFO)

2026-07-16 → 2026-07-19 • Direct • 3h

[Out: Fri 02:30 → Fri 05:30 • 3h] — [Stay: 3d 1h] — [Back: Mon 06:40 → Mon 09:40 • 3h]

WNSource: Aviasales (cached)

See more dates for SFO• Inserted 2026-06-06 · Sat 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 259

Updated ~1h agoExpires in ~2d

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MDW → San Francisco (SFO)

2026-07-16 → 2026-07-19 • Direct • 4h 30m

[Out: Fri 02:30 → Fri 07:00 • 4h 30m] — [Stay: 3d] — [Back: Mon 06:40 → Mon 11:10 • 4h 30m]

Source: Aviasales (cached)

See more dates for SFO• Inserted 2026-06-06 · Sat 07:00• Cached since 2026-06-06 · Sat 04:11• Synced 2026-06-06 · Sat 07:00

Est. USD 259

Cached ~0h agoExpires in ~2d

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MDW → DTT

2026-06-25 → 2026-07-23 • Direct • 3h

[Out: Thu 12:55 → Thu 15:55 • 3h] — [Stay: 28d 2h] — [Back: Thu 17:25 → Thu 20:25 • 3h]

WNSource: Aviasales (cached)

See more dates for DTT• Inserted 2026-06-05 · Fri 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 262

Updated ~25h agoExpires in ~23h

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MDW → Baltimore (BWI)

2026-07-07 → 2026-07-09 • Direct • 3h

[Out: Wed 24:35 → Wed 03:35 • 3h] — [Stay: 1d 21h] — [Back: Fri 01:00 → Fri 04:00 • 3h]

WNSource: Aviasales (cached)

See more dates for BWI• Inserted 2026-06-06 · Sat 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 267

Updated ~1h agoExpires in ~2d

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MDW → San Jose (SJC)

2026-07-16 → 2026-07-19 • Direct • 3h

[Out: Fri 01:50 → Fri 04:50 • 3h] — [Stay: 3d 2h] — [Back: Mon 06:55 → Mon 09:55 • 3h]

WNSource: Aviasales (cached)

See more dates for SJC• 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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MDW → Oakland (OAK)

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]

WNSource: Aviasales (cached)

See more dates for OAK• 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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MDW → San Jose (SJC)

2026-07-16 → 2026-07-19 • Direct • 4h 22m

[Out: Fri 01:50 → Fri 06:12 • 4h 22m] — [Stay: 3d 1h] — [Back: Mon 06:55 → Mon 11:18 • 4h 23m]

Source: Aviasales (cached)

See more dates for SJC• 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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MDW → Oakland (OAK)

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)

See more dates for OAK• 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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MDW → MKC

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

[Out: Tue 17:05 → Tue 18:30 • 1h 25m] — [Stay: 2d 4h] — [Back: Thu 22:35 → Fri 24:00 • 1h 25m]

Source: Aviasales (cached)

See more dates for MKC• Inserted 2026-06-06 · Sat 07:00• Cached since 2026-06-06 · Sat 02:45• Synced 2026-06-06 · Sat 07:00

Est. USD 338

Cached ~0h agoExpires in ~2d

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MDW → MKC

2026-07-07 → 2026-07-09 • Direct • 3h

[Out: Tue 17:05 → Tue 20:05 • 3h] — [Stay: 2d 3h] — [Back: Thu 22:35 → Fri 01:35 • 3h]

WNSource: Aviasales (cached)

See more dates for MKC• Inserted 2026-06-06 · Sat 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 338

Updated ~1h agoExpires in ~2d

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MDW → FMY

2026-06-30 → 2026-07-03 • Direct • 3h

[Out: Tue 23:55 → Wed 02:55 • 3h] — [Stay: 2d 6h] — [Back: Fri 09:10 → Fri 12:10 • 3h]

WNSource: Aviasales (cached)

See more dates for FMY• Inserted 2026-06-06 · Sat 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 340

Updated ~1h agoExpires in ~2d

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MDW → St. Louis (STL)

2026-07-17 → 2026-07-19 • Direct • 1h 7m

[Out: Fri 16:00 → Fri 17:07 • 1h 7m] — [Stay: 2d 5h] — [Back: Sun 21:40 → Sun 22:48 • 1h 8m]

Source: Aviasales (cached)

See more dates for STL• Inserted 2026-06-05 · Fri 01:00• Cached since 2026-06-05 · Fri 24:11• Synced 2026-06-06 · Sat 07:00

Est. USD 351

Cached ~30h agoExpires in ~18h

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MDW → St. Louis (STL)

2026-07-17 → 2026-07-19 • Direct • 3h

[Out: Fri 16:00 → Fri 19:00 • 3h] — [Stay: 2d 3h] — [Back: Sun 21:40 → Mon 24:40 • 3h]

WNSource: Aviasales (cached)

See more dates for STL• Inserted 2026-06-05 · Fri 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 351

Updated ~25h agoExpires in ~23h

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MDW → Nashville (BNA)

2026-07-03 → 2026-07-06 • Direct • 3h

[Out: Sat 02:40 → Sat 05:40 • 3h] — [Stay: 2d 22h] — [Back: Tue 03:35 → Tue 06:35 • 3h]

WNSource: Aviasales (cached)

See more dates for BNA• Inserted 2026-06-04 · Thu 18:00• Synced 2026-06-06 · Sat 07:00

Est. USD 358

Updated ~37h agoExpires in ~11h

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MDW → Charlotte (CLT)

2026-07-03 → 2026-07-06 • Direct • 1h 57m

[Out: Fri 23:55 → Sat 01:52 • 1h 57m] — [Stay: 2d 14h] — [Back: Mon 15:35 → Mon 17:33 • 1h 58m]

Source: Aviasales (cached)

See more dates for CLT• Inserted 2026-06-06 · Sat 07:00• Cached since 2026-06-04 · Thu 24:05• Synced 2026-06-06 · Sat 07:00

Est. USD 372

Cached ~0h agoExpires in ~24h

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MDW → Oakland (OAK)

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)

See more dates for OAK• 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 ~18h

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MDW → CMH

2026-06-24 → 2026-06-28 • Direct • 3h

[Out: Wed 20:15 → Wed 23:15 • 3h] — [Stay: 3d 14h] — [Back: Sun 13:00 → Sun 16:00 • 3h]

WNSource: Aviasales (cached)

See more dates for CMH• Inserted 2026-06-05 · Fri 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 391

Updated ~25h agoExpires in ~23h

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MDW → MLM

2026-08-29 → 2026-09-06 • Direct • 3h

[Out: Sat 19:32 → Sat 22:32 • 3h] — [Stay: 7d 15h] — [Back: Sun 13:14 → Sun 16:14 • 3h]

Y4Source: Aviasales (cached)

See more dates for MLM• Inserted 2026-06-06 · Sat 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 396

Updated ~1h agoExpires in ~2d

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MDW → MLM

2026-08-29 → 2026-09-06 • Direct • 4h

[Out: Sat 19:32 → Sat 23:32 • 4h] — [Stay: 7d 14h] — [Back: Sun 13:14 → Sun 17:14 • 4h]

Source: Aviasales (cached)

See more dates for MLM• Inserted 2026-06-06 · Sat 07:00• Cached since 2026-06-02 · Tue 02:07• Synced 2026-06-06 · Sat 07:00

Est. USD 396

Cached ~0h agoExpires in ~24h

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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 07:00

Est. USD 408

Updated ~25h agoExpires in ~23h

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MDW → BJX

2026-06-25 → 2026-07-18 • Direct • 3h 55m

[Out: Thu 20:29 → Fri 24:24 • 3h 55m] — [Stay: 22d 14h] — [Back: Sat 14:09 → Sat 18:04 • 3h 55m]

Source: Aviasales (cached)

See more dates for BJX• Inserted 2026-06-05 · Fri 01:00• Cached since 2026-06-04 · Thu 19:45• Synced 2026-06-06 · Sat 07:00

Est. USD 408

Cached ~30h agoExpires in ~18h

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MDW → EDWARD L LOGAN INTL (BOS)

2026-09-24 → 2026-09-27 • Direct • 3h

[Out: Thu 19:35 → Thu 22:35 • 3h] — [Stay: 2d 13h] — [Back: Sun 11:30 → Sun 14:30 • 3h]

WNSource: Aviasales (cached)

See more dates for BOS• Inserted 2026-06-06 · Sat 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 436

Updated ~1h agoExpires in ~2d

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MDW → VPS

2026-07-17 → 2026-07-19 • Direct • 3h

[Out: Sat 02:21 → Sat 05:21 • 3h] — [Stay: 1d 11h] — [Back: Sun 15:55 → Sun 18:55 • 3h]

G4Source: Aviasales (cached)

See more dates for VPS• Inserted 2026-06-06 · Sat 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 436

Updated ~1h agoExpires in ~2d

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MDW → BUF

2026-12-23 → 2026-12-28 • Direct • 1h 35m

[Out: Wed 19:10 → Wed 20:45 • 1h 35m] — [Stay: 5d] — [Back: Mon 20:20 → Mon 21:55 • 1h 35m]

Source: Aviasales (cached)

See more dates for BUF• Inserted 2026-06-05 · Fri 19:00• Cached since 2026-05-30 · Sat 24:00• Synced 2026-06-06 · Sat 07:00

Est. USD 494

Cached ~12h agoExpires in ~12h

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MDW → BUF

2026-12-24 → 2026-12-26 • Direct • 3h

[Out: Thu 19:30 → Thu 22:30 • 3h] — [Stay: 1d 15h] — [Back: Sat 13:00 → Sat 16:00 • 3h]

WNSource: Aviasales (cached)

See more dates for BUF• Inserted 2026-06-06 · Sat 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 525

Updated ~1h agoExpires in ~2d

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MDW → Cancún (CUN)

2026-06-15 → 2026-06-29 • Direct • 3h

[Out: Mon 14:55 → Mon 17:55 • 3h] — [Stay: 14d 3h] — [Back: Mon 21:10 → Tue 24:10 • 3h]

WNSource: Aviasales (cached)

See more dates for CUN• Inserted 2026-06-05 · Fri 06:00• Synced 2026-06-06 · Sat 07:00

Est. USD 555

Updated ~25h agoExpires in ~23h

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Price may differ at booking.