Chicago Cheap Flights

TRAVEL MORE FOR LESS

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 ❯

Austin

Texas

$80
Cheap flights to Austin in June to October for $80 roundtrip from Chicago
These deals uses at least 1 ULCC airline Dates available during an holiday period Direct flight
ORD-AUS
JUN-OCT

Mexico City

Mexico

$226
Cheap flights to Mexico City in August to March for $226 roundtrip from Chicago
Only limited dates at this price
ORD-MEX
AUG-MAR

Guatemala

Guatemala

$227
Cheap flights to Guatemala in September to January for $227 roundtrip from Chicago
These deals uses at least 1 ULCC airline
ORD-GUA
SEP-JAN

Barcelona

Spain

$298
Cheap flights to Barcelona in July to May for $298 roundtrip from Chicago
Dates available during an holiday period
ORD-BCN
JUL-MAY

Punta Cana

Dominican Republic

$319
Cheap flights to Punta Cana in August to September for $319 roundtrip from Chicago
These deals uses at least 1 ULCC airline Dates available during an holiday period
ORD-PUJ
AUG-SEP

Málaga

Spain

$387
Cheap flights to Málaga in August to December for $387 roundtrip from Chicago
These deals uses at least 1 ULCC airline Only limited dates at this price Dates available during an holiday period
ORD-AGP
AUG-DEC

London

United Kingdom

$392
Cheap flights to London in September to December for $392 roundtrip from Chicago
Only limited dates at this price Direct flight
MDW-LHR
SEP-DEC

Geneva

Switzerland

$447
Cheap flights to Geneva in August to December for $447 roundtrip from Chicago
Dates available during an holiday period
ORD-GVA
AUG-DEC

Bali

Indonesia

$502
Cheap flights to Bali in October to April for $502 roundtrip from Chicago
Only limited dates at this price
ORD-DPS
OCT-APR

Zhengzhou

China

$537
Cheap flights to Zhengzhou in November to January for $537 roundtrip from Chicago
ORD-CGO
NOV-JAN
LOAD MORE DEALS NOW
Show Less Deals

Travel Tips

GO TO OUR TRAVEL TIPS PAGE

Travel Inspiration

GO TO OUR INSPIRATION PAGE

Travel News

GO TO OUR TRAVEL NEWS PAGE

Flight Search Tool

GO TO OUR FLIGHT SEARCH PAGE

Hotel Search Tool

Booking.com
GO TO OUR HOTEL SEARCH PAGE

Car Rental Search Tool

GO TO OUR CAR RENTAL SEARCH PAGE

Other Travel Tools

Cruises

Tours &
Group Trips

Travel Insurance

Flight Delay Claims

MORE TO COME …

Thank you for using our links to support us at no cost to you!

SEE HOW ELSE TO HELP FOR FREE

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.

GO TO OUR ABOUT US PAGE
Cheap Flights

Flytrippers has been featured on:

Cheap Flights
Cheap Flights
Cheap Flights
Cheap Flights
Cheap Flights
Cheap Flights
FEATDD
Cheap Flights
Cheap Flights
Cheap Flights
Cheap Flights
FEAT12
×
×

Cart