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 22nd: deals are valid when posted but expire quickly.

New Orleans

Louisiana

$70

Cheap flights to New Orleans in October to February for $70 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

OCT-FEB

Atlanta

Georgia (USA)

$74

Cheap flights to Atlanta in November to December for $74 roundtrip from Chicago

ORD-ATL

NOV-DEC

Baltimore

Maryland

$96

Cheap flights to Baltimore in January to February for $96 roundtrip from Chicago

ORD-BWI

JAN-FEB

San Juan

Puerto Rico

$190

Cheap flights to San Juan in November to March for $190 roundtrip from Chicago

ORD-SJU

NOV-MAR

St. Thomas

US Virgin Islands

$238

Cheap flights to St. Thomas in December to February for $238 roundtrip from Chicago

ORD-STT

DEC-FEB

Medellín

Colombia

$336

Cheap flights to Medellín in November to March for $336 roundtrip from Chicago

ORD-MDE

NOV-MAR

Munich

Germany

$362

Cheap flights to Munich in November to March for $362 roundtrip from Chicago

ORD-MUC

NOV-MAR

London

England

$377

Cheap flights to London in January to February for $377 roundtrip from Chicago

ORD-LGW

JAN-FEB

Helsinki

Finland

$386

Cheap flights to Helsinki in March to June for $386 roundtrip from Chicago

ORD-HEL

MAR-JUN

Bilbao

Spain

$392

Cheap flights to Bilbao in December to February for $392 roundtrip from Chicago

ORD-BIO

DEC-FEB

Milan

Italy

$415

Cheap flights to Milan in December to March for $415 roundtrip from Chicago

ORD-MXP

DEC-MAR

Zhuhai

China

$447

Cheap flights to Zhuhai in January to March for $447 roundtrip from Chicago

ORD-ZUH

JAN-MAR

Riga

Latvia

$450

Cheap flights to Riga in January to March for $450 roundtrip from Chicago

ORD-RIX

JAN-MAR

Warsaw

Poland

$494

Cheap flights to Warsaw in November to December for $494 roundtrip from Chicago

ORD-WAW

NOV-DEC

Rome

Italy

$499

Cheap flights to Rome in November to July for $499 roundtrip from Chicago

ORD-FCO

NOV-JUL

Osaka

Japan

$515

Cheap flights to Osaka in January to August for $515 roundtrip from Chicago

ORD-KIX

JAN-AUG

Katowice

Poland

$538

Cheap flights to Katowice in January to March for $538 roundtrip from Chicago

MDW-KTW

JAN-MAR

Wrocław

Poland

$574

Cheap flights to Wrocław in November to March for $574 roundtrip from Chicago

MDW-WRO

NOV-MAR

Lviv

Ukraine

$577

Cheap flights to Lviv in November to September for $577 roundtrip from Chicago

ORD-LWO

NOV-SEP

Podgorica

Montenegro

$583

Cheap flights to Podgorica in March to May for $583 roundtrip from Chicago

ORD-TGD

MAR-MAY

Skopje

North Macedonia

$585

Cheap flights to Skopje in October to May for $585 roundtrip from Chicago

ORD-SKP

OCT-MAY

Lviv

Ukraine

$587

Cheap flights to Lviv in November to January for $587 roundtrip from Chicago

MDW-LWO

NOV-JAN

Kaohsiung

Taiwan

$645

Cheap flights to Kaohsiung in October to September for $645 roundtrip from Chicago

ORD-KHH

OCT-SEP

Santiago

Chile

$648

Cheap flights to Santiago in November to March for $648 roundtrip from Chicago

ORD-SCL

NOV-MAR

Lagos

Nigeria

$673

Cheap flights to Lagos in November to February for $673 roundtrip from Chicago

ORD-LOS

NOV-FEB

Bengaluru

India

$685

Cheap flights to Bengaluru in October to July for $685 roundtrip from Chicago

ORD-BLR

OCT-JUL

Muscat

Oman

$696

Cheap flights to Muscat in March to April for $696 roundtrip from Chicago

ORD-MCT

MAR-APR

Johannesburg

South Africa

$746

Cheap flights to Johannesburg in October to May for $746 roundtrip from Chicago

MDW-JNB

OCT-MAY

Accra

Ghana

Mauritius

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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.