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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Spotted February 27th: deals are valid when posted but expire quickly.

The deals with the COVID19 Refund icon are bookable through OTAs or airlines that allow for free cancellation or changes.

⚠ WARNING: Travel during the pandemic involves many risks. Click here to consider all of them thoroughly.

Filter by dates, destinations, and free changes


2021

2022

Region

Flexibility

Fort Myers

Florida

$32
Chicago to Fort Myers flights
These deals uses at least 1 ULCC airline Direct flight Lowest price we have ever seen! These deals uses at least 1 airline that do not allow free regular carry-on
ORD-RSW
MAR-MAY

New York

New York

$66
Chicago to New York flights
These deals uses at least 1 ULCC airline Only limited dates at this price Weekend Gateway Lowest price we have ever seen! These deals uses at least 1 airline that do not allow free regular carry-on
ORD-EWR
APRIL

Mérida

Mexico

$184
Chicago to Mérida flights
Only limited dates at this price
ORD-MID
MAR-MAY

Hyderabad

India

$606
Chicago to Hyderabad flights
Lowest price we have ever seen!
ORD-HYD
FEB-OCT

Batumi

Georgia

$837
Chicago to Batumi flights
Only limited dates at this price
ORD-BUS
MAY-JUN
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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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