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Chicago flight deals.

The latest flight drops published on @roamdrops.chi, from O'Hare and Midway.

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Chicago flight deals from @roamdrops.chi, with the fares and travel dates as posted.

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Published Chicago to Fort-de-France flight deal: $639
@roamdrops.chi
Chicago (ORD)

Fort-de-FranceFDF

Fare when posted$639

Travel datesDec 6, 2026 – Dec 15, 2026

Original Instagram caption

Chicago (ORD) → Fort-de-France (FDF) — $639 Travel: Dec 6, 2026 – Dec 15, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to Fort-de-FranceAviasales ↗
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Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Mombasa flight deal: $999
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Chicago (ORD)

MombasaMBA

Fare when posted$999

Travel datesDec 3, 2026 – Dec 10, 2026

Original Instagram caption

Chicago (ORD) → Mombasa (MBA) — $999 Travel: Dec 3, 2026 – Dec 10, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to MombasaAviasales ↗
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Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Birmingham flight deal: $219
@roamdrops.chi
Chicago (MDW)

BirminghamBHM

Fare when posted$219

Travel datesNov 5, 2026 – Nov 11, 2026

Original Instagram caption

Chicago (MDW) → Birmingham (BHM) — $219 Travel: Nov 5, 2026 – Nov 11, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to BirminghamAviasales ↗
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Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to San Juan flight deal: $188
@roamdrops.chi
Chicago (ORD)

San JuanSJU

Fare when posted$188

Travel datesDec 12, 2026 – Dec 18, 2026

Original Instagram caption

Chicago (ORD) → San Juan (SJU) — $188 Travel: Dec 12, 2026 – Dec 18, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to San JuanAviasales ↗
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Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Bucharest flight deal: $624
@roamdrops.chi
Chicago (ORD)

BucharestOTP

Fare when posted$624

Travel datesDec 5, 2026 – Dec 11, 2026

Original Instagram caption

Chicago (ORD) → Bucharest (OTP) — $624 Travel: Dec 5, 2026 – Dec 11, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to BucharestAviasales ↗
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Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Samarkand flight deal: $850
@roamdrops.chi
Chicago (ORD)

SamarkandSKD

Fare when posted$850

Travel datesNov 2, 2026 – Nov 10, 2026

Original Instagram caption

Chicago (ORD) → Samarkand (SKD) — $850 Travel: Nov 2, 2026 – Nov 10, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to SamarkandAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Chengdu flight deal: $899
@roamdrops.chi
Chicago (ORD)

ChengduTFU

Fare when posted$899

Travel datesMar 22, 2027 – Mar 31, 2027

Original Instagram caption

Chicago (ORD) → Chengdu (TFU) — $899 Travel: Mar 22, 2027 – Mar 31, 2027 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to ChengduAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Puerto Natales flight deal: $1117
@roamdrops.chi
Chicago (ORD)

Puerto NatalesPNT

Fare when posted$1117

Travel datesDec 4, 2026 – Dec 10, 2026

Original Instagram caption

Chicago (ORD) → Puerto Natales (PNT) — $1117 Travel: Dec 4, 2026 – Dec 10, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to Puerto NatalesAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Chengdu flight deal: $899
@roamdrops.chi
Chicago (ORD)

ChengduTFU

Fare when posted$899

Travel datesMar 22, 2027 – Mar 31, 2027

Original Instagram caption

Chicago (ORD) → Chengdu (TFU) — $899 Travel: Mar 22, 2027 – Mar 31, 2027 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to ChengduAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗

Prices shown are the fares shared in the original posts, not a new live quote. Fares and availability can change; verify dates, baggage and booking conditions before purchasing.