Chicago to Nashville — Halloween Weekend for $39 Round Trip!

f you’ve been waiting for a reason to sneak away this fall, this might be it. Flights from Chicago to Nashville are currently available for just $39 round trip, perfectly timed for Halloween weekend or a quick autumn getaway. That’s an incredible deal — well below the historical average of $130+ for this route.

Whether you’re headed down for the live music and neon lights of Broadway, a Titans game, or pumpkin-spiced everything at local coffee spots like Barista Parlor, Nashville delivers big fall vibes with small-town warmth.

Even better, there are several other dates through October and November available at or near this same $39 price point.

The Flights