Chicago, Chicago river, Illinois

Visit the Windy City with Nonstop Flights ✈️ 🌆

Nonstop Flights to Chicago from $98 Round Trip with Legacy Airlines

from $98

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Pirates, are you a deep-dish pizza kind of person? Travel to Chicago with these budget-friendly nonstop flights to Chicago with JetBlue & Legacy Airlines, starting as low as $98 round-trip with departure cities from both coasts.


  • 🚀 Nonstop


  • Boston
  • New York
  • Seattle
  • Portland
  • Los Angeles
  • San Francisco
  • Las Vegas
  • Philadelphia
  • Denver
  • Houston
  • Orlando
  • Charlotte
  • Raleigh


  • Chicago
  • Illinois


Here are some of the dates and departure airports we found for you, but more are available.

These flights and prices are based on nonstop journeys.

All prices listed are from Legacy Airlines but there is more availability in other airlines like Spirit and Frontier.

Click on the links below to change your departure city and date.

🔻 Departing from Boston

🔻 Departing from Seattle

🔻 Departing from New York

🔻 Departing from Charlotte

🔻 Departing from Portland

🔻 Departing from Raleigh

🔻 Departing from Philadelphia

🔻 Departing from Denver

🔻 Departing from Houston

🔻 Departing from Orlando

🔻 Departing from Los Angeles

🔻 Departing from San Francisco

🔻 Departing from Las Vegas

Example of Cheapest Flight

Other Options

Also looking for a place to stay? Try our Hotel Booking tool or check one of our Chicago deals below.

Additional Information

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*All of our deals are available at the time of publishing, but prices are subject to fluctuate and change at any time.