$26 Cheap Flights from Chicago

One-way

Departing from

Going to

Departing from

Chicago

Going to

anywhere

New York (EWR)

United States • January, 2026

88% AI deal score

$440 $29

Mexico City (MEX)

Mexico • January, 2026

86% AI deal score

$240 $26

New Orleans (MSY)

United States • January, 2026

83% AI deal score

$180 $39

Guadalajara (GDL)

Mexico • January, 2026

83% AI deal score

$225 $42

Top Destinations Where Can You Fly from Chicago

Cheap flights from Chicago

New York, United States

TOP

Jan • Direct

$440

$29

-$411

93%

Mexico City, Mexico

TOP

Jan • Direct

$240

$26

-$214

89%

Orlando, United States

TOP

Jan • Direct

$205

$29

-$176

86%

Orlando, United States

TOP

Feb • Direct

$205

$29

-$176

86%

Orlando, United States

TOP

Feb • Direct

$205

$29

-$176

86%

Miami, United States

TOP

Mar • Direct

$233

$29

-$204

88%

Find flights from Chicago to anywhere

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Looking for inspiration on destinations? Here are some popular flight deals from Chicago one-way fares:

Mexico City, Mexico - from $26 (direct)

Las Vegas, United States - from $29 (direct)

Charlotte, United States - from $29 (direct)

New York, United States - from $29 (direct)

Houston, United States - from $29 (direct)

Dallas, United States - from $29 (direct)

Washington, D.C., United States - from $29 (direct)

Tampa, United States - from $29 (direct)

Phoenix, United States - from $29 (direct)

Philadelphia, United States - from $29 (direct)

See more destinations you can fly to from Chicago – anywhere in the world at the best prices.

See More Destinations

Facts About Flights from Chicago

Nearby airport(s)

Chicago Midway International (MDW)

Chicago, United States

O Hare International (ORD)

Chicago, United States

Chicago Rockford International (RFD)

Chicago, United States

Insights for flights from Chicago

Cheapest route found

$45

Recent fare for flights from Chicago.

Cheapest month to fly

January

Average fares are lowest in this month.

Typical price range (round-trip)

50$ - 600$

For economy class tickets from Chicago, found in the last week.

Most popular airlines from Chicago

American Airlines

Alaska Airlines, Inc.

JetBlue Airways

Delta Air Lines

ORD Airport Deal Stats

Current most discounted routes

ORD - Rajkot

90% OFF

ORD - Dortmund

89% OFF

ORD - Tirupati

88% OFF

Avg. most discounted routes (last 3 months)

ORD - Saarbrücken

88% OFF

ORD - Szymany, Szczytno County

87% OFF

ORD - Rennes

87% OFF

ORD airport insights

Best days to catch a deal

Wednesday, Saturday

For the best flight deals from O'Hare International Airport, consider searching on Wednesdays, when the highest number of deals are typically found. Conversely, Mondays and Tuesdays tend to have fewer deals available from O'Hare.

Avg. deal survival time

19.2 hours

Deals from O'Hare International Airport typically last for an average of 19.2 hours. This means that on average, flight deals departing from O'Hare are available for purchase for less than a day.

Rare deal frequency

3 deals

We uncovered 3 rare flight deals originating from O Hare International airport in the last month. These deals, scoring 90+ on our AI Deal Score, typically represent mistake fares, exclusive promotions, or significant price reductions.

Average price drop

-80%

Deals originating from O Hare International airport see an average price drop of 80.2%. Travelers can save significantly on flights by monitoring deals from O Hare International airport.

Next 4 weeks: deal forecast

O'Hare Flight Forecast - February 2026

Based on current trends, flight deals from O'Hare International are expected to remain stable next month. There are no significant price drops or increases anticipated for flights originating from O'Hare in February 2026.

Top 5 biggest price drops (last 3 months)

Found on December 28

ORD - Rajkot

$3,675 → $378

90%

Found on December 27

ORD - Dortmund

$3,125 → $343

89%

Found on December 28

ORD - Tirupati

$3,100 → $368

88%

Found on December 29

ORD - Saarbrücken

$5,800 → $699

88%

Found on December 27

ORD - Szymany, Szczytno County

$3,425 → $446

87%

Check these nearby airports too

Looking for more options? These airports near ORD sometimes drop rare deals too:

Gerald R. Ford International (GRR)

~6 rare deals/month

General Mitchell International (MKE)

~3 rare deals/month

Chicago Rockford International (RFD)

~6 rare deals/month

If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially GRR and MKE for long-haul deal surprises.

Travel Trends: Popular Destinations from Chicago

Every month, we analyze search and booking data to see where travelers from Chicago are heading. Here are the current hot destinations from Chicago:

Top domestic destinations

Orlando

TOP

Chicago

Las Vegas

TOP

Chicago

Miami

TOP

Chicago

These cities are seeing the most searches and bookings from Chicago this month.

Top international destinations

London

TOP

United Kingdom

Rome

TOP

Italy

Travelers from Chicago are flocking here, possibly due to seasonal events or great deals.

Travel trend insight

Travelers from Chicago are increasingly drawn to destinations with rich history and cultural experiences. London and Rome remain popular due to their iconic landmarks, historical significance, and vibrant cultural scenes, offering diverse attractions for a wide range of travelers.

Booking Flights from Chicago: Frequently Asked Questions

Flight costs from Chicago can vary wildly depending on your destination, the time of year, and how far in advance you book. A short domestic flight might cost as little as $50-$150, while international flights can range from $500 to upwards of $2000 or even more for premium classes. Keep in mind that prices fluctuate based on demand, so flexibility is your friend. I would recommend using RatePunk Flights Search, where you can set flexible dates, and RatePunk will show you the best deals.

To snag the best deals, be flexible with your travel dates and consider flying on weekdays (Tuesday and Wednesday are often cheapest). Booking in advance (2-3 months for domestic, 3-6 months for international) can also save you money. Set up fare alerts to track price changes and consider budget airlines that fly from Chicago for more affordable options. And don’t forget to check for deals on connecting flights, sometimes a layover can save you a bundle.

Generally, the sweet spot for cheaper flights from Chicago is during the shoulder seasons (spring and fall). Avoid peak travel times like summer and holidays, when prices surge due to high demand. January and February (excluding holiday weekends) are often the most budget-friendly months. Flying mid-week is almost always cheaper than flying on the weekends, and red-eye flights, while less convenient, can save you some serious cash.

Pro Tips for Finding Cheap Flights from Chicago

Finding the cheapest airfare from Chicago is easier if you use a few smart strategies. Here are our top tips to help you score a great deal:

Be Flexible with Dates: Wiggle room with your travel dates can lead to sweet savings. Mid-week flights or traveling during the shoulder season (spring/fall) often means lower prices, leaving you with extra cash for deep-dish pizza in Chicago!

Set Destination to 'Anywhere': Feeling adventurous? Set your destination to 'Anywhere' on flight search engines. You might stumble upon an unbelievably cheap flight to a destination you've never considered, opening up a world of new experiences.

Explore More Destinations from Chicago

Looking for more options? Here are some popular routes and related travel deals:

Flights from Chicago to Amsterdam - Find cheap flights from Chicago to AMS

Flights from Chicago to Madrid - Find cheap flights from Chicago to MAD

Cheap flights to Chicago - Searching for cheap flights to Chicago? (Great for fiends/family visiting you, or return trips.)

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$26 Cheap Flights from Chicago

Top Destinations Where Can You Fly from Chicago

Cheap flights from Chicago

New York, United States

$29

Mexico City, Mexico

$26

Orlando, United States

$29

Orlando, United States

$29

Orlando, United States

$29

Miami, United States

$29

Find flights from Chicago to anywhere

Facts About Flights from Chicago

Nearby airport(s)

Chicago Midway International (MDW)

O Hare International (ORD)

Chicago Rockford International (RFD)

Insights for flights from Chicago

$45

January

50$ - 600$

Most popular airlines from Chicago

ORD Airport Deal Stats

Current most discounted routes

Avg. most discounted routes (last 3 months)

ORD airport insights

Wednesday, Saturday

19.2 hours

3 deals

-80%

O'Hare Flight Forecast - February 2026

Top 5 biggest price drops (last 3 months)

ORD - Rajkot

ORD - Dortmund

ORD - Tirupati

ORD - Saarbrücken

ORD - Szymany, Szczytno County

Check these nearby airports too

Gerald R. Ford International (GRR)

General Mitchell International (MKE)

Chicago Rockford International (RFD)

Travel Trends: Popular Destinations from Chicago

Top domestic destinations

Orlando

Las Vegas

Miami

Top international destinations

London

Rome

Travel trend insight

Booking Flights from Chicago: Frequently Asked Questions

How much does it typically cost to fly from Chicago?

How much does it typically cost to fly from Chicago?

What are some tips for booking cheap flights from Chicago?

What are some tips for booking cheap flights from Chicago?

When is the best time to fly out of Chicago to get the lowest fares?

When is the best time to fly out of Chicago to get the lowest fares?

Which airports in Chicago offer the most flight options?

Which airports in Chicago offer the most flight options?

What are some popular international destinations with direct flights from Chicago?

What are some popular international destinations with direct flights from Chicago?

Are there any alternative airports near Chicago I should consider for better deals?

Are there any alternative airports near Chicago I should consider for better deals?

Pro Tips for Finding Cheap Flights from Chicago

Explore More Destinations from Chicago

Search more flights

Complete your trip

Most popular destinations from Chicago

What travel documents are required for international flights from Chicago?

What travel documents are required for international flights from Chicago?

How early should I arrive at the airport for a flight from Chicago?

How early should I arrive at the airport for a flight from Chicago?

What are some common factors that affect flight prices from Chicago?