Chicago Cheap Flights

TRAVEL MORE FOR LESS

Amazing flight deals and great travel content, curated just for you.

Today's Best Flight Deals From Chicago

How Flight Deals Work
These are deals, so there are a few important things you need to understand. Slide to read more ❯
We Only Spot Deals
To get a heavily discounted flight (often 50% off), you need to be flexible and fly on the dates that are on sale.
Deals Change Every Day
The dates and destinations that are on sale change every single day, so check back often.
All Deals Expire Quickly
These prices are so good that they are usually gone in a matter of hours, not days. So act fast!
Roundtrip $USD Prices
These deals are always for roundtrips, prices include all mandatory taxes and are quoted in $USD.
Easy-To-Use Links
We don't sell flights so we provide convenient links to the best online booking sites (thanks for using our links)
ULCC & LD Tags
Ultra Low-Cost Carrier deals with bag restrictions and deals with very Limited Dates are clearly marked.
Want more details ?
Check out our page that explains how flight deals work.
Learn more ❯
Spotted February 11th: deals are valid when posted but expire quickly.

Rome

Italy

$639
Cheap flights to Rome in May to August for $639 roundtrip from Chicago
Only limited dates at this price Direct flight
ORD-FCO
MAY-AUG

Dhaka

Bangladesh

$736
Cheap flights to Dhaka in July to November for $736 roundtrip from Chicago
Only limited dates at this price Direct flight
ORD-DAC
JUL-NOV
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About Flytrippers

Our mission is simple: we want to help you travel more, for less.

We are Andrew and Kevin, two friends who both wanted to travel more (without breaking the bank). So we learned to spot flight deals, to find cheaper flights… and also many other tips along the way. Now we’re sharing them, so you too can explore the world more often.

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