ORDChicagoBLRBangaloreDXBDubaiSINSingaporeSFOSan FranciscoJFKNew YorkDELNew Delhi
Chicago flight deals to destinations around the world

Fares worth leaving town for

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Handpicked round-trip flight deals from ORD to the places you keep saving.

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This week’s drops

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Europe pick1 stop
ORDChicago
LISLisbon
from$398round trip
Travel windowNov 5–13, 2026

Eight nights for tiled streets, late dinners and Atlantic light.

Or with points
39,800 pts398 pts39,800 miles
Portal baseline at 1¢/point · transfer-partner awards may require fewer points
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Long-haul steal1 stop
ORDChicago
HNDTokyo
from$684round trip
Travel windowJan 18–27, 2027

Nine nights of neon, ramen counters and crisp winter mornings.

Or with points
68,400 pts684 pts68,400 miles
Portal baseline at 1¢/point · transfer-partner awards may require fewer points
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Long weekendNonstop
ORDChicago
MEXMexico City
from$287round trip
Travel windowOct 22–26, 2026

Four days for galleries, tacos and a very good reason to take Friday off.

Or with points
28,700 pts287 pts28,700 miles
Portal baseline at 1¢/point · transfer-partner awards may require fewer points
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Winter escapeNonstop
ORDChicago
SJUSan Juan
from$241round trip
Travel windowFeb 6–11, 2027

Trade the lakefront wind for five warm nights by the Caribbean.

Or with points
24,100 pts241 pts24,100 miles
Portal baseline at 1¢/point · transfer-partner awards may require fewer points
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One tap from inspiration

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  1. 01

    Catch the drop on @roamdrop.chicago

  2. 02

    Open the bio link and find the deal

  3. 03

    Check live options with the booking partner