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 ❯
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Bozeman

Montana

$142
Cheap flights to Bozeman in January to February for $142 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price These deals uses at least 1 airline that do not allow free regular carry-on
ORD-BZN
JAN-FEB

Helsinki

Finland

$382
Cheap flights to Helsinki in January to October for $382 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price Dates available during an holiday period
ORD-HEL
JAN-OCT

Zurich

Switzerland

$468
Cheap flights to Zurich in January to August for $468 roundtrip from Chicago
These deals uses at least 1 ULCC airline Dates available during an holiday period
ORD-ZRH
JAN-AUG

Düsseldorf

Germany

$471
Cheap flights to Düsseldorf in December to September for $471 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price Dates available during an holiday period Dates available during the Christmas holiday period
ORD-DUS
DEC-SEP

Kailua-Kona

Hawaii

$485
Cheap flights to Kailua-Kona in January to March for $485 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price These deals uses at least 1 airline that do not allow free regular carry-on
ORD-KOA
JAN-MAR

Tokyo

Japan

$492
Cheap flights to Tokyo in January to February for $492 roundtrip from Chicago
Only limited dates at this price Lowest price we have ever seen!
ORD-NRT
JAN-FEB

Honolulu

Hawaii

$499
Cheap flights to Honolulu in January to March for $499 roundtrip from Chicago
Only limited dates at this price
MDW-HNL
JAN-MAR

Marseille

France

$510
Cheap flights to Marseille in February to August for $510 roundtrip from Chicago
These deals uses at least 1 ULCC airline Dates available during an holiday period These deals uses at least 1 airline that do not allow free regular carry-on
ORD-MRS
FEB-AUG

Catania

Italy

$524
Cheap flights to Catania in July to October for $524 roundtrip from Chicago
These deals uses at least 1 ULCC airline Dates available during an holiday period These deals uses at least 1 airline that do not allow free regular carry-on
ORD-CTA
JUL-OCT

Hilo

Hawaii

$548
Cheap flights to Hilo in April to June for $548 roundtrip from Chicago
ORD-ITO
APR-JUN

Osaka

Japan

$553
Cheap flights to Osaka in February to July for $553 roundtrip from Chicago
Dates available during an holiday period
ORD-KIX
FEB-JUL

Kuwait

Kuwait

$566
Cheap flights to Kuwait in February to June for $566 roundtrip from Chicago
ORD-KWI
FEB-JUN

Chisinau

Moldova

$615
Cheap flights to Chisinau in January to July for $615 roundtrip from Chicago
These deals uses at least 1 ULCC airline Dates available during an holiday period These deals uses at least 1 airline that do not allow free regular carry-on
ORD-KIV
JAN-JUL

São Paulo

Brazil

$628
Cheap flights to São Paulo in December to August for $628 roundtrip from Chicago
Dates available during an holiday period
ORD-GRU
DEC-AUG

Adana

Turkey

$720
Cheap flights to Adana in January to April for $720 roundtrip from Chicago
Only limited dates at this price
ORD-ADA
JAN-APR

Malé

Maldives

$723
Cheap flights to Malé in February to September for $723 roundtrip from Chicago
These deals uses at least 1 ULCC airline Dates available during an holiday period These deals uses at least 1 airline that do not allow free regular carry-on
ORD-MLE
FEB-SEP

Erbil

Iraq

$757
Cheap flights to Erbil in March to April for $757 roundtrip from Chicago
ORD-EBL
MAR-APR

Melbourne

Australia

$831
Cheap flights to Melbourne in February to November for $831 roundtrip from Chicago
Only limited dates at this price
ORD-MEL
FEB-NOV
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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.

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