Chicago: CHEAP FLIGHTS (AND MORE)

Your destination for amazing flight deals... and great travel content to inspire you and to help you travel more for less.

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 the details)

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

DIR, V, W Tags

Even better deals with direct flights, Vacation time dates or Weekend escapes clearly marked

Want more details ?

Check out our page that explains how flight deals work

Learn more ❯

Spotted January 16th: deals are valid when posted but expire quickly.

Cancun

Mexico

$192

Cheap flights to Cancun in January to February for $192 roundtrip from Chicago

ORD-CUN

JAN-FEB

Barcelona

Spain

$318

Cheap flights to Barcelona in May for $318 roundtrip from Chicago

ORD-BCN

MAY

Algiers

Algeria

$475

Cheap flights to Algiers in January for $475 roundtrip from Chicago

ORD-ALG

JANUARY

Conakry

Guinea

$640

ORD-CKY

FEBRUARY

Conakry

Guinea

$668

Cheap flights to Conakry in February for $668 roundtrip from Chicago

MDW-CKY

FEBRUARY

Rio de Janeiro

Brazil

$792

ORD-GIG

JANUARY

Cotonou

Benin

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About Flytrippers

Our mission is simple: help & inspire you to 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, we learned Travel Hacking… and also many other tips along the way. Now we’re sharing them, so you too can explore the world more often.