Hotels in Uptown Chicago: 2024 Best Deals

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This contemporary Chicago bed and breakfast offers urban decor and modern comforts. The courteous staff will accommodate your needs while giving you plenty of space to decompress. Enjoy freshly baked biscuits every morning and cozy common areas to relax. After a long day exploring the Windy City, come home to House 5863! Details
TripAdvisor user rating 3.50 out of 5
72 Reviews
$196.50 $157.50
You Save: $39.00 /night

If you find yourself journeying to the majestic city of Chicago, the bustling uptown district is a splendid choice to rest your head. And let me tell you, the hotels in this neck of the woods, they're an experience in themselves. Rich with character and dripping with charm, they replicate the very soul of Uptown Chicago, artistically reflecting its robust history and vibrant culture.

Picture this: you're waking up to breathtaking cityscape views, the morning light glinting off soaring skyscrapers, and the lively murmurs of the Windy City coming to life. The accommodation is plush, adorned with modern amenities to perfect your stay - think comfortable beds that you sink into after a long day, luxe toiletries to pamper yourself, and top-notch service that makes you feel like royalty. And let's not forget about the food – a gastronomic gala that's like a slice of Chicago on a plate.

Beyond the confines of the hotel, you're in the heart of a district that offers everything. From iconic theatres, tantalising food joints, to quaint boutiques - Uptown Chicago does not disappoint.

As the day winds down, the hotels become your serene escape from the city's hustle and bustle. Their lounges offer intriguing meet-up spaces, and their bars, the ideal spot to sip a cocktail as the city lights twinkle outside. The fusion of warm ambiance and unparalleled service creates a comforting cocoon that's hard to say goodbye to when your stay comes to an end.

Whether it's a quick weekend getaway or an extended business trip, staying at a hotel in the Uptown district truly encapsulates the essence of Chicago. A balance between anonymity and friendliness, comfort and sophistication, modernity and antiquity, it's a taste of the city that leaves a lasting impression.

Experience the Best of Uptown Chicago: Secure Your Comfort with Tripster!


With amenities ranging from state-of-the-art fitness centers to top-tier dining options right at the hotel premises, choosing to stay in this district is a delightful experience on its own. Your visit will not only offer a comfortable stay but also provide an immersion into the rich cultural heritage synonymous with Uptown Chicago. Rest assured, your choice to vacation or do business in these Chicago hotels will only enhance your experience.