Delta has roundtrip flights from Chicago to Key West priced at just $177 for travel March through May, and then again August through December. That’s an incredible fare for a route that almost never dips this low — the only time I’ve seen it cheaper was back in May of 2023, when it briefly hit $175.
Key West is one of those destinations that feels like a true escape without needing a passport. Visitors love wandering Duval Street, catching the sunset celebration at Mallory Square, snorkeling and boating in crystal-clear waters, and soaking up the laid-back island vibe that makes everything slow down a notch.
One major highlight: Dry Tortugas National Park. Located about 70 miles west of Key West, it’s home to Fort Jefferson, turquoise water, and some of the best snorkeling in Florida. It’s one of the most unique national parks in the U.S. and absolutely worth the boat or seaplane trip.
At $177 roundtrip on Delta, this is one of the best opportunities you’ll see to get to Key West in 2025 — whether you’re chasing spring sunshine or planning a late-season island escape.
The Flights
