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 ❯

With the evolution of the coronavirus situation, we have decided to suspend all our flight deal postings indefinitely. We still have a lot of articles for you to read while you are at home and will continue to update you on the situation daily.

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October 10, 2020

Flytrippers’ Interview On “Every Passport Stamp” Video Q&A Series

September 25, 2020

20 Pictures From Our First Week Traveling In Over 4 Months

August 16, 2020

Here Is Where The Famous Bus From “Into the Wild” Will Be Relocated

August 12, 2020

This New Plane Seat Concept Is Designed For Post-Coronavirus Air Travel

April 22, 2020

Incredible Deal: Free Flights To This Amazing Country In 2021 To Restart Tourism

April 1, 2020

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Activities & Attractions

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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.