Perfect Long Weekend in Chicago 🎡 3 Nights with Flights

Ready to give your passport a little break? How about a long weekend in the Windy City! We found a 3-night stay in Chicago from just $217 including flights.

Your home base will be the Millennium Hotel Knickerbocker Chicago (3.9/5 on TripAdvisor), a classic gem with plenty of character. Just steps from the Magnificent Mile, you’ll have more than 400 retailers, restaurants, and high-end shops at your fingertips—perfect for exploring the city or even getting a head start on holiday shopping.

And here’s the kicker: the hotel once housed a speakeasy run by the Capone family, adding a dash of intrigue to your stay. When you’re not out exploring, take advantage of the on-site gym and spa for a little R&R.

Pirate Tip: While the best prices we found were for January, For a few dollars more you can check out Chicago in October and November.

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All of our deals are available at the time of publishing, but prices are subject to fluctuations and changes at any time.

Photos from Booking

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