Chicago Cheap Flights

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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 December 11th: deals are valid when posted but expire quickly.

Tampa

Florida

$62
Cheap flights to Tampa in January to March for $62 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price Direct flight
ORD-TPA
JAN-MAR

Palm Springs

California

$66
Cheap flights to Palm Springs in December to February for $66 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price
ORD-PSP
DEC-FEB

New York

New York

$81
Cheap flights to New York in December to February for $81 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price
ORD-LGA
DEC-FEB

Boston

Massachusetts

$136
Cheap flights to Boston in January to March for $136 roundtrip from Chicago
ORD-BOS
JAN-MAR

Mexico City

Mexico

$237
Cheap flights to Mexico City in February to July for $237 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price
ORD-MEX
FEB-JUL

Los Cabos

Mexico

$265
Cheap flights to Los Cabos in January to July for $265 roundtrip from Chicago
Only limited dates at this price Direct flight
ORD-SJD
JAN-JUL

London

United Kingdom

$287
Cheap flights to London in January to November for $287 roundtrip from Chicago
Only limited dates at this price Direct flight
ORD-LHR
JAN-NOV

London

United Kingdom

$300
Cheap flights to London in December to August for $300 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price
ORD-LGW
DEC-AUG

San José

Costa Rica

$325
Cheap flights to San José in March to November for $325 roundtrip from Chicago
Only limited dates at this price Direct flight
ORD-SJO
MAR-NOV

Gothenburg

Sweden

$337
Cheap flights to Gothenburg in January to February for $337 roundtrip from Chicago
These deals uses at least 1 ULCC airline
ORD-GOT
JAN-FEB

Cartagena

Colombia

$371
Cheap flights to Cartagena in March to July for $371 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price Direct flight
ORD-CTG
MAR-JUL

Málaga

Spain

$410
Cheap flights to Málaga in March to September for $410 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price Direct flight
ORD-AGP
MAR-SEP

Kahului

Hawaii

$493
Cheap flights to Kahului in January to July for $493 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price Direct flight
ORD-OGG
JAN-JUL

Aqaba

Jordan

$495
Cheap flights to Aqaba in January to February for $495 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price
ORD-AQJ
JAN-FEB

Honolulu

Hawaii

$504
Cheap flights to Honolulu in January to May for $504 roundtrip from Chicago
Only limited dates at this price Direct flight
ORD-HNL
JAN-MAY

Nagoya

Japan

$510
Cheap flights to Nagoya in February to March for $510 roundtrip from Chicago
ORD-NGO
FEB-MAR

Osaka

Japan

$548
Cheap flights to Osaka in January to March for $548 roundtrip from Chicago
Direct flight
ORD-KIX
JAN-MAR

Sofia

Bulgaria

$548
Cheap flights to Sofia in March to October for $548 roundtrip from Chicago
These deals uses at least 1 ULCC airline Direct flight
ORD-SOF
MAR-OCT

Bangkok

Thailand

$555
Cheap flights to Bangkok in January to July for $555 roundtrip from Chicago
Only limited dates at this price Direct flight
ORD-BKK
JAN-JUL

Casablanca

Morocco

$621
Cheap flights to Casablanca in January to April for $621 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price Direct flight
ORD-CMN
JAN-APR

Phnom Penh

Cambodia

$656
Cheap flights to Phnom Penh in January to November for $656 roundtrip from Chicago
Only limited dates at this price Direct flight
ORD-PNH
JAN-NOV

Bali

Indonesia

$678
Cheap flights to Bali in May to November for $678 roundtrip from Chicago
Direct flight
ORD-DPS
MAY-NOV

Hyderabad

India

$794
Cheap flights to Hyderabad in March to August for $794 roundtrip from Chicago
Direct flight
ORD-HYD
MAR-AUG
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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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