Expired This offer has expired. American’s Chicago companion deal had to be booked by Nov. 4, 2026. Trips already booked at the discounted fare keep it as long as everyone stays on the same reservation. For live offers, see our current deals.
Flying to or from Chicago this winter with someone? American’s Chicago fares page is running a companion deal: up to 20% off the base fare for each companion when 2 to 9 people book First together on one reservation. It works on select flights between Chicago O’Hare (ORD) and select cities in the lower 48. You have to book by Nov. 4, 2026 at 11:59 p.m. Central, for travel Nov. 1, 2026 through Feb. 28, 2027. A few catches: the first traveler pays full price, the discount varies by route and doesn’t touch taxes or fees, and it only works on flights American and American Eagle operate (no codeshares). It doesn’t combine with other promos, and it can’t be added to a trip you’ve already booked. The blackout dates cover the big holiday days: Nov. 20 and 28-30, Dec. 18-19 and 26-28, and Jan. 2-4. Everyone also has to stay on the same reservation, because if someone cancels or drops off, the fare can be repriced. To use it, search First on aa.com with all your travelers on one booking, check that the companion fare shows the discount before you pay, and use a card that earns extra on airfare. Related: American's No-Fee MileUp Card at $100 Plus 15,000 Miles, Citi's AAdvantage Business Card at 75,000 Miles, Free 15,000 American Miles With Code GET15K and Best Airline Miles for Beginners. More deals at Points Quest.