Signing up for credit cards through partner links earns us a commission. Here’s our full Advertising Policy.
Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers.
Fly to Chicago for ~$80 round-trip from Boston, Dallas, New York, or Los Angeles this fall!
This deal is moving fast so book now!
How to Book It
Link: ITA Matrix
Link: Google Flights
Here’s how to use Google Flights to find sale dates.
I found fares between New York and Chicago in September for ~$80 round-trip in coach.
You can fly to Chicago from:
- Los Angeles
- New York
I was able to find non-stop flights from Dallas to Chicago for ~$81.
Terms and Conditions
Note: You can hold a reservation on American Airlines for up to 24 hours and get a full refund if you change your mind.
And if you book a ticket with an online travel agency like Orbitz or Expedia, you may be eligible for a refund within a short time of booking your ticket. Check out my post on cancellation policies for airlines and online travel agencies for more details!
Boston or Los Angeles to Chicago
Boston or Los Angeles to Chicago flights are available on United Airlines from September to November 18, 2015. You must depart on Tuesday, Wednesday, or Saturday. And tickets must be purchased 21 days in advance.
Boston to Chicago is also available from April to May 2016 with the same terms.
New York to Chicago
New York to Chicago flights are available on American Airlines or United Airlines from September to early November 2015. You must depart Tuesday, Wednesday, or Saturday. Both airlines require a 7-day advance purchase.
Dallas to Chicago
Dallas to Chicago on American Airlines is available from late August to early November 2015. You must depart on Tuesday, Wednesday or Saturday, and buy your ticket 21 days in advance.
What If You’re Not in 1 of These Cities?
Southwest – If you need more Southwest points, Chase Ultimate Rewards points transfer to Southwest. Plus, if you have the Southwest Companion Pass, a friend can fly with you for (almost) free!
British Airways – If you’re a short flight away from an included city, you can save miles by using British Airways Avios points to book an award flight on American Airlines.
And you’ll get the 1st bag checked free for yourself and up to 8 travel companions on American Airlines with the Citi AAdvantage Executive World Elite Mastercard or Barclays Aviator card (not available for new sign-ups). You do NOT have to use the card to pay for your ticket!
Get Free Hotel Nights With These Cards
If you book a cheap flight, remember there are lots of ways to get cheap or free hotel rooms with points from credit card bonuses and spending!
Remember, you can transfer flexible points like Chase Ultimate Rewards or American Express Membership Rewards to different hotel programs.
Note: Folks who want to book paid stays could check out discount sites like Orbitz, Expedia, or TravelPony for deals. But remember you won’t get stay credits or points (and might not have your elite status recognized).
And if you’re feeling adventurous or prefer a neighborhood feel, Airbnb is a great way to save money on accommodations, especially for longer stays.
Read my tips on how to negotiate a better price on Airbnb!
~$80 for a round-trip ticket to Chicago is a terrific deal!
If you’re looking for a quick getaway, this a fantastic opportunity. Fares will sell out fast!
Remember to check the terms from your city, because each 1 has slightly different dates and purchase requirements.
Let me know if you visit The Windy City!