City deals & social drops

Chicago flight deals.

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

THE WEEKLY NEWSLETTER

Get the next drop.

Great flight deals from your city, straight to your inbox.

DTWDetroitORD / MDWChicagoBLRBangaloreDXBDubaiSINSingaporeSFOSan FranciscoJFKNew YorkDELNew Delhi

AS SEEN ON INSTAGRAM

Same drops. One place.

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

Follow @roamdrops.chi
Auto-updates every minuteLast checked
Published Chicago to Santiago de Querétaro flight deal: $271
@roamdrops.chi
Chicago (ORD)

Santiago de QuerétaroQRO

Fare when posted$271

Travel datesMar 25, 2027 – Apr 3, 2027

Original Instagram caption

Chicago (ORD) → Santiago de Querétaro (QRO) — $271 Travel: Mar 25, 2027 – Apr 3, 2027 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to Santiago de QuerétaroAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Gold Coast flight deal: $1345
@roamdrops.chi
Chicago (ORD)

Gold CoastOOL

Fare when posted$1345

Travel datesDec 7, 2026 – Dec 13, 2026

Original Instagram caption

Chicago (ORD) → Gold Coast (OOL) — $1345 Travel: Dec 7, 2026 – Dec 13, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to Gold CoastAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Tuxtla Gutiérrez flight deal: $293
@roamdrops.chi
Chicago (ORD)

Tuxtla GutiérrezTGZ

Fare when posted$293

Travel datesNov 30, 2026 – Dec 6, 2026

Original Instagram caption

Chicago (ORD) → Tuxtla Gutiérrez (TGZ) — $293 Travel: Nov 30, 2026 – Dec 6, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to Tuxtla GutiérrezAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Hobart flight deal: $1432
@roamdrops.chi
Chicago (ORD)

HobartHBA

Fare when posted$1432

Travel datesDec 13, 2026 – Dec 19, 2026

Original Instagram caption

Chicago (ORD) → Hobart (HBA) — $1432 Travel: Dec 13, 2026 – Dec 19, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to HobartAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Ponce flight deal: $340
@roamdrops.chi
Chicago (ORD)

PoncePSE

Fare when posted$340

Travel datesDec 12, 2026 – Dec 21, 2026

Original Instagram caption

Chicago (ORD) → Ponce (PSE) — $340 Travel: Dec 12, 2026 – Dec 21, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to PonceAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Rovaniemi flight deal: $773
@roamdrops.chi
Chicago (ORD)

RovaniemiRVN

Fare when posted$773

Travel datesDec 7, 2026 – Dec 15, 2026

Original Instagram caption

Chicago (ORD) → Rovaniemi (RVN) — $773 Travel: Dec 7, 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 RovaniemiAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Auckland flight deal: $1106
@roamdrops.chi
Chicago (ORD)

AucklandAKL

Fare when posted$1106

Travel datesOct 25, 2026 – Nov 2, 2026

Original Instagram caption

Chicago (ORD) → Auckland (AKL) — $1106 Travel: Oct 25, 2026 – Nov 2, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to AucklandAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Fort Myers flight deal: $118
@roamdrops.chi
Chicago (ORD)

Fort MyersRSW

Fare when posted$118

Travel datesDec 7, 2026 – Dec 13, 2026

Original Instagram caption

Chicago (ORD) → Fort Myers (RSW) — $118 Travel: Dec 7, 2026 – Dec 13, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to Fort MyersAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Yangon flight deal: $908
@roamdrops.chi
Chicago (ORD)

YangonRGN

Fare when posted$908

Travel datesJan 14, 2027 – Jan 21, 2027

Original Instagram caption

Chicago (ORD) → Yangon (RGN) — $908 Travel: Jan 14, 2027 – Jan 21, 2027 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to YangonAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Guam flight deal: $1305
@roamdrops.chi
Chicago (ORD)

GuamGUM

Fare when posted$1305

Travel datesJan 14, 2027 – Jan 22, 2027

Original Instagram caption

Chicago (ORD) → Guam (GUM) — $1305 Travel: Jan 14, 2027 – Jan 22, 2027 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to GuamAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Evansville flight deal: $261
@roamdrops.chi
Chicago (ORD)

EvansvilleEVV

Fare when posted$261

Travel datesNov 14, 2026 – Nov 21, 2026

Original Instagram caption

Chicago (ORD) → Evansville (EVV) — $261 Travel: Nov 14, 2026 – Nov 21, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to EvansvilleAviasales ↗
Partner link
More travel options
Flights Kiwi.com ↗Things to do Klook ↗eSIM Yesim ↗
Published Chicago to Paramaribo flight deal: $717
@roamdrops.chi
Chicago (ORD)

ParamariboPBM

Fare when posted$717

Travel datesNov 7, 2026 – Nov 13, 2026

Original Instagram caption

Chicago (ORD) → Paramaribo (PBM) — $717 Travel: Nov 7, 2026 – Nov 13, 2026 Fares and availability can change. #ChicagoTravel #FlightDeals #ChicagoFlights #TravelDeals #RoamDrops

View Instagram post ↗Check current fare on Google Flights ↗
Book flights to ParamariboAviasales ↗
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.