Chicago Cheap Flights

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 October 20th: deals are valid when posted but expire quickly.

Austin

Texas

$96

Cheap flights to Austin in February to March for $96 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-AUS

FEB-MAR

Los Cabos

Mexico

$254

Cheap flights to Los Cabos in January to June for $254 roundtrip from Chicago

ORD-SJD

JAN-JUN

Cali

Colombia

$274

Cheap flights to Cali in October to December for $274 roundtrip from Chicago

ORD-CLO

OCT-DEC

Beijing

China

$354

Cheap flights to Beijing in November to April for $354 roundtrip from Chicago

ORD-PEK

NOV-APR

Tallinn

Estonia

$359

Cheap flights to Tallinn in December to April for $359 roundtrip from Chicago

ORD-TLL

DEC-APR

Vilnius

Lithuania

$361

Cheap flights to Vilnius in November to May for $361 roundtrip from Chicago

ORD-VNO

NOV-MAY

Stuttgart

Germany

$362

Cheap flights to Stuttgart in November to April for $362 roundtrip from Chicago

ORD-STR

NOV-APR

Manchester

England

$364

Cheap flights to Manchester in November to March for $364 roundtrip from Chicago

ORD-MAN

NOV-MAR

Athens

Greece

$365

Cheap flights to Athens in February to April for $365 roundtrip from Chicago

ORD-ATH

FEB-APR

Wrocław

Poland

$373

Cheap flights to Wrocław in December to May for $373 roundtrip from Chicago

ORD-WRO

DEC-MAY

London

England

$375

Cheap flights to London in December to September for $375 roundtrip from Chicago

ORD-LGW

DEC-SEP

Lima

Peru

$376

Cheap flights to Lima in October to May for $376 roundtrip from Chicago

ORD-LIM

OCT-MAY

Kraków

Poland

$385

Cheap flights to Kraków in November to August for $385 roundtrip from Chicago

ORD-KRK

NOV-AUG

Rome

Italy

$403

Cheap flights to Rome in October to August for $403 roundtrip from Chicago

ORD-FCO

OCT-AUG

Vientiane

Laos

$406

Cheap flights to Vientiane in November to March for $406 roundtrip from Chicago

ORD-VTE

NOV-MAR

Chiang Mai

Thailand

$437

Cheap flights to Chiang Mai in October to March for $437 roundtrip from Chicago

ORD-CNX

OCT-MAR

Mandalay

Myanmar

$443

Cheap flights to Mandalay in January to February for $443 roundtrip from Chicago

ORD-MDL

JAN-FEB

Hong Kong

China

$486

Cheap flights to Hong Kong in October to April for $486 roundtrip from Chicago

ORD-HKG

OCT-APR

Phnom Penh

Cambodia

$507

Cheap flights to Phnom Penh in October to February for $507 roundtrip from Chicago

ORD-PNH

OCT-FEB

Jakarta

Indonesia

$514

Cheap flights to Jakarta in November for $514 roundtrip from Chicago

ORD-CGK

NOVEMBER

Naples

Italy

$534

Cheap flights to Naples in April to October for $534 roundtrip from Chicago

ORD-NAP

APR-OCT

Palermo

Italy

$550

Cheap flights to Palermo in November to May for $550 roundtrip from Chicago

ORD-PMO

NOV-MAY

Sofia

Bulgaria

$588

Cheap flights to Sofia in April to May for $588 roundtrip from Chicago

ORD-SOF

APR-MAY

Dubai-Sharjah

United Arab Emirates

$640

Cheap flights to Dubai-Sharjah in November to January for $640 roundtrip from Chicago

ORD-SHJ

NOV-JAN

Lagos

Nigeria

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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.