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Architecture, Building, Chicago
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How Ya' Bean 🫘Chicago🍕

Pet Friendly 🐕4-Night Break from $244 Including Air ✈️💖

From $244

Published by
Katrina Kerr·12/23/2023

Hey Pirates – check out this 4-night stay in the heart of Chicago. Hotel Saint Clair – Magnificent Mile (4/5 on Trip Advisor) is a European-style boutique hotel rising 16 stories above the Windy City that is pet friendly. Spend a long weekend with flights from $244 per person. Normally flights alone are over $200.

Steps from everything, the hotel puts you close to Chicago’s biggest attractions, like the Navy Pier, Shedd Aquarium, and Michigan Avenue Shopping.


Family Friendly
Flights included
Free Extras
Free Wifi
Great Food
Great for Couples
Great for Groups
Great for Solo Travel
Kids Friendly
See All Highlights


  • Boston
  • New York City
  • Miami
  • Washington
  • Dallas
  • Las Vegas
  • Phoenix
  • Los Angeles
  • San Francisco
  • Seattle


  • Chicago


Here are some of the dates and departure airports we found for you, but there are many more available.

These fares are based on short layovers or nonstop journeys.

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

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City TripsFamily-FriendlyFoodieFree ExtrasMini BreakPet-FriendlyRomanticSolo TravelUnder 500WinterWinter Break
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