A Chicago itinerary for a luxury weekend through a city of unexpected gems and beauty.
Even though dubbed ‘The Windy City’ Chicago is a lively city that has so much to offer all year round. The perfect place for city life, luxury, romance, history, and more.
Keep reading as we share our Chicago travel guide perfect for a luxury weekend in Chicago, IL.
Luxury Weekend in Chicago:
MOMENTS OF TRAVEL
- A private and independent itinerary perfect for those looking to indulge in luxury and private tours exploring all of Chicago.
- Discover the beauty of the city from new heights, relax with ancient baths, and what a true rooftop brunch experience in compasses.
- Highlights include lake shore jogs, enjoying the music along the riverwalk, lounging around the most gorgeous rooftop pool, and shopping along Mag mile.
BEAUTIFUL STAYS
ABOVE: The Langham Hotel Chicago is one of the most notable luxury hotels in the industry. Langham offers incredible views of the city with a contemporary style that has a sophisticated luxury vibe. Even more amazing is the jacuzzi, spa, and pool onsite. We’d love to upgrade your stay with complimentary breakfast and hotel credit. Suggested stay 2 nights minimum.
BELOW: Viceroy Hotel Chicago (pictured left) is a Gold Coast favorite over-looking Lake Michigan with impeccable service and style! Lounge around this hotel’s rooftop, morning or night for beautiful city views. We can’t forget to mention…#petfriendlyhotel. Four Seasons Hotel Chicago (pictured right) is located just steps from the heart of it all. And is equipped with everything you may need from a Martini man to a pristine pool, a children’s program, and more. Email us and ask about upgrades available! Suggested stay 2 nights minimum each.
PLACES TO EXPLORE & THINGS TO DO IN CHICAGO
Searching for amazing things to do for your luxury weekend in Chicago, tmd Escapes has you covered. Our top 5 things to do in Chicago and make it private:
- Best of Chicago Trio: Skydeck, River Cruise, Walking Tour
- Private Chicago Tour By Helicopter
- Private VIP Speakeasy Cocktail Tour
- Guided Chicago Food Tasting Tour
- Private Photoshoot
- More
Even more, things to do in Chicago:
FOOD & WINE
BOOK YOUR ESCAPE
Customize this Chicago travel guide with us at tmd Escapes to include everything you want for your Chicago itinerary. From booking the perfect stay to renting a car for your trip or even securing your restaurant and activities in advance — we have you covered.
For more weekend escapes or to book hotels or upgrade to private tours and transfers, get in touch with us today.
We’re excited to help you escape the ordinary!
Ready to indulge in a luxury-filled weekend in Chicago? Get in touch for a personalized quote today.
TRAVEL ESSENTIALS
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