American Airlines Round-Trip From New York City to Chicago Starting At $99

If you want a chance to travel to Florida, here’s a great opportunity for you! If so, you can get a round-trip flight with American Airlines New York City to Chicago starting at $99. Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline bristling with skyscrapers such as the iconic John Hancock Center, sleek, 1,451-ft. Willis Tower and neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute and its expansive collections, including noted Impressionist works. Take advantage of this flight deal and book your flight today!

We recommend you look up your preferred dates on Google Flights in case there is a cheaper price than the ones we listed. Depending when you book, the prices can change! (YMMV) The airline fares rule associated with your flight and be reviewed over pre-purchase, on your contract, and post purchase with the itinerary displayed on their website, be sure you read their full terms before making your purchase.

Flights from New York City to Chicago

• Buy It Now
• Promotion: Round-trip from New York City to Chicago $99

Flights from Chicago to New York City

• Buy It Now
• Promotion: Round-trip from Chicago to New York City $99

• Valid: Valid for travel on the outbound from many Wednesdays from October through December 2017.

How To Get LGA/ORD Flight Deal:

1. Use Priceline to check the flights and times that fit best for you. We recommend selecting United Airlines since their prices seem to be the cheapest. (YMMV)
2. To earn cash back we highly recommend using the above, Best Airline Flight Credit Cards, to save the most money.
3. Once you found the times that you would like to make sure you book it early so that it doesn’t change.

Bottom Line:

Don’t miss out on the chance to see New York’s beautiful city night lights or the infamous bean in downtown Chicago. It’s a great opportunity to escape from your home and treat yourself to a nice vacation. US citizens should visit the US Passports & International Travel website for the latest information, including exercising safety abroad and entry requirements. This is the cheapest fare I found but please let us know if you got anything different! If you want more Cheap Flight Deals, check out our master list!

United ClubSM Infinite Card Click here to learn how to apply