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 February 26th: deals are valid when posted but expire quickly.

New Orleans

Louisiana

$64

Cheap flights to New Orleans in March to May for $64 roundtrip from Chicago

These deals uses at least 1 ULCC airline

These deals uses at least 1 airline that do not allow free regular carry-on

ORD-MSY

MAR-MAY

Philadelphia

Pennsylvania

$76

Cheap flights to Philadelphia in May to July for $76 roundtrip from Chicago

Dates available during an holiday period

ORD-PHL

MAY-JUL

Rome

Italy

$279

Cheap flights to Rome in March to January for $279 roundtrip from Chicago

ORD-FCO

MAR-JAN

Lisbon

Portugal

$326

Cheap flights to Lisbon in March to January for $326 roundtrip from Chicago

ORD-LIS

MAR-JAN

Bogota

Colombia

$337

Cheap flights to Bogota in April to September for $337 roundtrip from Chicago

ORD-BOG

APR-SEP

Algiers

Algeria

$458

Cheap flights to Algiers in March to August for $458 roundtrip from Chicago

ORD-ALG

MAR-AUG

Toulouse

France

$471

Cheap flights to Toulouse in August to October for $471 roundtrip from Chicago

ORD-TLS

AUG-OCT

Casablanca

Morocco

$486

Cheap flights to Casablanca in March to October for $486 roundtrip from Chicago

ORD-CMN

MAR-OCT

Mykonos

Greece

$495

Cheap flights to Mykonos in April to September for $495 roundtrip from Chicago

ORD-JMK

APR-SEP

Sofia

Bulgaria

$498

Cheap flights to Sofia in August to October for $498 roundtrip from Chicago

ORD-SOF

AUG-OCT

Bratislava

Slovakia

$524

Cheap flights to Bratislava in May to June for $524 roundtrip from Chicago

ORD-BTS

MAY-JUN

Chiang Mai

Thailand

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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.