A Chicago escape full of big moments
4 nights from £1,739 per person based on 2 sharing
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Settle into Staypineapple - An Iconic Hotel in The Loop, where playful design meets modern comfort. Your Deluxe Two Doubles room comes with buttery-soft bedding, smart TVs and bright, characterful touches that make every corner feel unique. With extras like unlimited filtered water, speedy Wi-Fi, and those famously fluffy robes, this boutique base really nails the art of easy living. Step outside and you’re moments from Millennium Park, the Art Institute, and the buzzing energy of State Street.
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Take things up a level with a visit to 360 Chicago, perched on the 94th floor of the John Hancock Centre. The views stretch across four states, and for a proper adrenaline rush, the “Tilt” experience lets you lean out over Michigan Avenue for an unforgettable new perspective on the city.
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Then comes one of the trip’s true highlights: an evening at the United Centre cheering on the Chicago Blackhawks. Feel the crack of sticks on ice, the rush of the crowd, and the unbeatable buzz of a live NHL game. Whether you’re a hockey fan or not, it’s the kind of experience that leaves you grinning for days.
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And of course, no visit would be complete without sampling Chicago’s unbeatable food scene. Tuck into that famous deep-dish pizza at Lou Malnati’s, grab a drink and some live blues at Buddy Guy’s Legends, or wander the West Loop for small, independent spots serving everything from Korean barbecue to craft doughnuts.
What’s included:
• 4 nights at Staypineapple – An Iconic Hotel in The Loop
• Deluxe Two Doubles Room; room only basis
• Entrance to 360 Chicago Observatory
• Tickets to a Chicago Blackhawks NHL Ice Hockey game at the United Center (Upper Goal seating on 02/02)
• Flight (Premium) from London Heathrow on 31/01/2026; with private transfers
• Trip includes 1 overnight flight, please speak to your Travel Counsellor for further details
Terms and Conditions
Subject to availability. Please give me a call for further details. Price based on two adults sharing. Prices correct at time of posting. Offers are subject to change. I can advise on travel insurance at the time of booking.
4 nights from £1,739 per person based on 2 sharing
The Small Print
These offers are brought to you by Travel Counsellors Ltd and all are ATOL protected by the Civil Aviation Authority. Where we have created the package ourselves, the holiday offer will be covered under our own ATOL. Our ATOL number is 6751. Where the offer has been sourced through another tour operator, it will be protected under that tour operator's ATOL. Full details on the individual ATOL protection that applies to each holiday offer will be given at time of booking. Prices and information contained in this page are correct at the time of distribution, are subject to availability and can be withdrawn or amended at any time without notice to you. Prices shown may be subject to departure tax, ticket on departure or a passenger APC charge. Please ask your Travel Counsellor at the time of booking.
