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 ❯

Spotted November 15th: deals are valid when posted but expire quickly.

Reykjavik

Iceland

$200

Cheap flights to Reykjavik in November to December for $200 roundtrip from Chicago

These deals uses at least 1 ULCC airline

ORD-KEF

NOV-DEC

Mexico City

Mexico

Pro Tip: The “Secret” Handrail To Help You Walk Down The Aisle Of A Plane

Andrew D'Amours November 13, 2018

How To Pay With A Canadian Credit Card At US Gas Pumps

Andrew D'Amours November 9, 2018

A Map Of The World’s Population Divided Into 10 Equal Sections

Andrew D'Amours November 15, 2018

9 Amazing Warm Destinations You Can Fly To For Free If You Win Our Giveaway

Andrew D'Amours November 9, 2018

Here’s What It Was Like Onboard The Inaugural Flight With Swoop, Canada’s New Ultra Low-Cost Carrier

Andrew D'Amours November 7, 2018

Air Canada Pilots Blamed For What “Could Not Have Gotten Literally Or Figuratively Any Closer To A Major Disaster”

Andrew D'Amours September 27, 2018

Flight Delay Claims

GO TO OUR OTHER TRAVEL TOOLS PAGES

MORE TO COME …

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

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.

TRAVEL MORE FOR LESS

Today's Best Flight Deals From Chicago

Travel Tips

Pro Tip: The “Secret” Handrail To Help You Walk Down The Aisle Of A Plane

How To Pay With A Canadian Credit Card At US Gas Pumps

Travel Inspiration

A Map Of The World’s Population Divided Into 10 Equal Sections

9 Amazing Warm Destinations You Can Fly To For Free If You Win Our Giveaway

Travel News

Here’s What It Was Like Onboard The Inaugural Flight With Swoop, Canada’s New Ultra Low-Cost Carrier

Air Canada Pilots Blamed For What “Could Not Have Gotten Literally Or Figuratively Any Closer To A Major Disaster”

Flight Search Tool

Hotel Search Tool

Car Rental Search Tool

Other Travel Tools

Cruises

Tours &
Group Trips

Travel Insurance

Flight Delay Claims

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

About Flytrippers

Flytrippers has been featured on:

TRAVEL MORE FOR LESS

Today's Best Flight Deals From Chicago

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

About Flytrippers

Flytrippers has been featured on:

Cart