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We spent 24 hours in Chicago before flying to Paris using points and miles, staying at the Intercontinental Magnificent Mile and exploring the city with our three kids. This strategic positioning flight saved us points while giving us an exciting mini-vacation in Chicago with deep dish pizza, the Bean, and activities like the Ice Cream Museum.

• Booked Chicago to Paris for 85,000 Flying Blue points for all five family members
• Used Southwest credits and gift cards for the positioning flight from Phoenix
• Stayed at the Intercontinental Magnificent Mile using a free night certificate
• Received a room upgrade thanks to IHG Platinum Elite status
• Kids enjoyed the hotel's indoor pool movie night with popcorn and lemonade
• Visited Chicago highlights: Lou Malnati's deep dish pizza, the Bean, and Starbucks Reserve
• Ice Cream Museum was expensive but memorable for the children
• Ed Debevic's restaurant with intentionally rude servers was entertaining
• Positioning flights can be cost-effective when traveling as a family
• Using hotel night certificates makes layovers more comfortable and fun

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