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!
Via The Flight Deal, American Airlines and United Airlines have tickets on sale for travel from September through early November. And certain cities have more dates available!
You can search for this fare using ITA Matrix or Google Flights, then book it on the American Airlines or United Airlines website.
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:
- Boston
- Dallas
- 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
Link: The Flight Deal Fare Page
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
Link: The Flight Deal Fare Page
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
Link: The Flight Deal Fare Page
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.
Chase Ultimate Rewards points , American Express Membership Rewards points, and Starwood Preferred Guest points transfer to British Airways.
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
Link: Hot Deals – Hotel Credit 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!
To find hotels that can be booked with points, I like using Hotel Hustle (which even shows you if rooms are actually available!) or AwardMapper.
Remember, you can transfer flexible points like Chase Ultimate Rewards or American Express Membership Rewards to different hotel programs.
Check out my posts on all the ways to earn Hilton and Hyatt points!
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!
Bottom Line
~$80 for a round-trip ticket to Chicago is a terrific deal!
Folks from Boston, Dallas, Los Angeles, or New York can fly to Chicago on American Airlines or United Airlines this fall, which is a great time to visit!
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!
Thanks for the tip! Last night I booked 2 r/t tickets for a Saturday-Tuesday September from NYC to ORD for only $160.40 total! Yowsa!
I got 108 R/t from FT lauderdale I booked on Sunday
I am going there on American to ORD
I am retuning on southwest from Midway
I paid 54 each way!!
I am leaving sat 8/29 returning tues 9/1
I was going to book American both ways but last minute decided to check southwest and I prefered their schedule because they depart midway at 2:50 pm. (All the $54 American and United retuns were at 6 am!!)
It looks like they are all competing which is good for us consumers
Also I usually don’t fly southwest because from FLL they are always highest in price to everywhere this might be good for a long trip with luggage but I’m only going for a few days. But looks like they wanted in on the competition as well
Great deal – I love Chicago! We’ve stayed at the Intercontinental (on points), the Homewood Suites (on points), and theWit ($150 off deal last year), and they were all fantastic. It’s great walking around the city, going to parks, riding bikes, seeing the planetarium… Just a really great city.