Chicago/Begin Historic Route 66 Top Hotel Picks
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| # | Hotel | Stars | Rating | Reviews | Distance |
|---|---|---|---|---|---|
| 1 | InterContinental Chicago Magnificent Mile | ★★★★★ | 4.2 | 25 | 1.29 km |
| 2 | Kimpton Gray Hotel | ★★★★ | 4.4 | 2 | 0.59 km |
| 3 | Holiday Inn Chicago Dwtn - the Mart | ★★★ | 4.4 | 13 | 1.46 km |
| 4 | Crowne Plaza Chicago West Loop | ★★★ | 4.3 | 11 | 1.84 km |
| 5 | Voco Chicago Downtown - Riverwalk by IHG | ★★★ | 4.2 | 6 | 1.46 km |
| 6 | Holiday Inn & Suites Chicago-Downtown | ★★★ | 4.2 | 8 | 1.37 km |
| 7 | Holiday Inn Express Chicago - Magnificent Mile | ★★ | 4.3 | 12 | 1.6 km |
Nestled in the heart of Chicago's Magnificent Mile, this luxurious hotel seamlessly blends historic charm with modern elegance. Housed in the former Medinah Athletic Club from 1929, every detail exudes sophistication. Sip fine wines at ENO, unwind by the gold-leaf walls, or take a dip in the legendary pool once used by actor Johnny Weissmuller. The surrounding area is equally captivating, with Navy Pier, Shedd Aquarium, and Oak Street Beach just minutes away. Whether for business meetings or romantic weddings, this hotel offers everything you need for an unforgettable stay.
Everything you need to know about Begin Historic Route 66
Near the Route 66 Start Sign in Chicago, Hyatt House Chicago Downtown is a top choice, offering modern rooms and complimentary breakfast just steps from Michigan Avenue. Its central location provides easy access to the historic Route 66 landmark and downtown attractions. Another excellent option is The Dearborn Hotel, known for its classic architecture and prime proximity to the start point. Both hotels feature convenient public transit links, making them ideal bases for exploring Chicago’s rich road-trip heritage and urban charm.
From downtown Chicago, take the CTA Blue Line to Roosevelt Station, then transfer to a bus or walk about 10 minutes to reach the Route 66 Start Sign. Alternatively, rent a car and drive south along Lake Shore Drive, a scenic route that takes around 20 minutes. This stretch offers beautiful views and marks the perfect beginning of your "American Road Trip" journey. Use a map app for accurate navigation to the iconic sign.
Near the Route 66 Start Sign, enjoy taking photos at the Chicago Riverwalk with the iconic highway marker as backdrop, and explore the Museum of Science and Industry to learn about the history of America’s famed road. Join a local Route 66-themed tour bus to dive into the cultural legends of the "Mother Road." In the evening, stroll along Navy Pier for stunning city lights and a vibrant atmosphere—perfect for capturing the spirit of the American road trip.
Yes, it’s highly suitable for families. The Route 66 Start Sign is located in downtown Chicago, close to family-friendly attractions like Navy Pier, Chicago Children's Museum, and several green spaces. Parents can enjoy strolling along the Riverwalk, taking a boat ride, or visiting the Museum of Science and Industry for interactive exhibits. The area is flat, safe, and well-connected, making it an ideal first stop for a family road trip across America.
The best photo spot is directly in front of the Route 66 Start Sign on Michigan Avenue, framed by the Chicago skyline and the iconic yellow sign. Visit during early morning or golden hour for soft lighting and enhanced image quality. For a dramatic long-exposure shot, walk south along Lake Shore Drive and use a telephoto lens to capture the road stretching into the distance. Use a tripod for sharp, stable images, especially in low light.
Yes! Intelligentsia Coffee in the West Loop is a top-rated specialty café offering expertly brewed pour-overs and locally roasted beans in a stylish setting. Another great option is Dolce Vita Coffee in River North, featuring outdoor seating with views of the Chicago River. Both cafés provide a relaxed, artistic vibe—perfect for slowing down and savoring a moment of urban calm while soaking in the essence of Chicago’s creative spirit.
See what other travelers say about Begin Historic Route 66
Staying at the InterContinental Chicago Magnificent Mile was an absolute delight from start to finish. The location is unbeatable—right on the Magnificent Mile, with easy access to shopping, dining, and attractions. I loved how stylish and modern the hotel feels, from the elegant lobby to the well-designed rooms. My room was spotless, spacious, and perfectly equipped with everything I needed—comfortable bed, excellent lighting, high-speed Wi-Fi, and a bathroom that felt like a spa. The staff went above and beyond with their friendly and professional service; they remembered my name and even offered local tips that made my trip more enjoyable. Breakfast was a highlight—fresh, delicious, and varied, with standout items like the house-made pastries and locally sourced eggs. The attention to detail in cleanliness, safety, and overall guest experience truly sets this hotel apart. If you're visiting Chicago, this is the place to stay. A perfect blend of luxury, convenience, and warmth.
The ground-floor restaurant makes dining effortless—no need to leave the hotel even if you don’t want to eat in-house. The room was spacious and incredibly comfortable, making the stay truly enjoyable. With easy access to downtown via public transit, it’s a perfect choice for travelers who value convenience and quality. I’d definitely book again.
Arrived late at night only to be told there was no room available despite having booked two months in advance. The manager mentioned they tried contacting me during the day, but I never received any call. After some back-and-forth, I was offered a single-bed room instead of the twin-bed one I originally reserved — not ideal, especially after such a long wait. However, after discussing with the platform, I was able to get the first night’s stay waived as compensation. Overall, the hotel’s location is excellent — right in the heart of Magnificent Mile, walking distance to shopping, dining, and attractions. The lounge on the 15th floor is a nice spot to unwind with drinks or a light meal. The room itself is spacious, the bed is comfortable, and the bathtub makes for a relaxing end to the day. Despite the initial check-in hiccup, the staff were polite and responsive. It’s a solid choice if you’re looking for convenience and a good base in downtown Chicago.
I’ve stayed here multiple times and always impressed by the consistent room cleaning service—daily, on time, and with excellent standards. In a country where hotel cleanliness can be hit or miss, this level of reliability is truly rare and appreciated. The breakfast is a classic American-style spread: solid choices, warm coffee, fresh fruit, and good pastries. It’s not fancy, but it’s satisfying and fills you up for the day. Located just steps from the subway, getting around downtown Chicago is super convenient. I’d definitely recommend this hotel for business travelers or anyone visiting the West Loop area who values consistency, comfort, and easy access to transit.
Staying at Voco Chicago Downtown - Riverwalk by IHG was an absolute delight. The room was spacious and well-designed, offering plenty of comfort and a great sense of openness. Breakfast was fantastic—fresh, delicious, and with a wide variety of options to choose from. Best part? The hotel is just steps away from the iconic Riverwalk. I spent a few relaxing evenings walking along the riverfront, enjoying the city lights and lively atmosphere. The location is unbeatable, and the overall experience was top-notch. From the thoughtful touches in the room to the friendly staff, every detail made me feel welcome. If you're visiting downtown Chicago, this hotel is a must-try for both convenience and charm.
I absolutely loved my stay at Holiday Inn & Suites Chicago-Downtown! The location is unbeatable—just a short walk from downtown attractions and easily accessible via public transit. The hotel itself was clean, well-maintained, and felt modern throughout. What really stood out was the front desk staff—they were incredibly friendly, helpful, and made me feel welcome from the moment I arrived. Their warm hospitality truly made a difference. Plus, the price was super affordable for the quality and convenience offered. I’d definitely book here again if I’m back in Chicago. Highly recommend!
I can't recommend this Holiday Inn Express Chicago - Magnificent Mile enough. The location is unbeatable—right across from Trader Joe's, so grocery shopping is a breeze. It's just a 7-8 minute walk to Trump Tower, and less than 20 minutes to Millennium Park. From there, it's only a few more minutes to the shores of Lake Michigan—perfect for a relaxing evening stroll. The front desk staff were incredibly friendly and helpful. We arrived at 10 AM, and even though check-in wasn't available yet, they gladly stored our luggage at no extra cost. When we returned around 2:30 PM, we were told to wait about 25 minutes. But instead of leaving us waiting in limbo, the staff actually came to check on us—and discovered a room was already ready! They apologized and made sure we were taken care of right away. While the amenities aren't flashy, the rooms are clean, comfortable, and well-maintained. For the price and convenience, this place offers outstanding value. I’ll definitely be back if I ever visit Chicago again.
Staying at the JW Marriott Chicago was an absolute highlight of my trip to the city. From the moment I walked in, the elegant ambiance and modern design set the tone for a truly memorable experience. The rooms are immaculately clean—every corner, every surface, spotless. The beds were incredibly comfortable, and the bathroom felt like a spa with top-notch fixtures and thoughtful touches. Everything is brand new and well-maintained, which really adds to the luxury feel. The staff went above and beyond—friendly, attentive, and always ready to help with anything I needed, from local recommendations to transportation arrangements. Location-wise, it's super convenient; just a short walk to downtown attractions and public transit stops. Whether you're visiting for business or leisure, this hotel delivers exceptional value. It’s not just a place to stay—it’s an experience. I’ll definitely book here again next time I’m in Chicago.
Staying at Waldorf Astoria Chicago was an absolute delight from start to finish. The suite featured a beautiful fireplace, and the front desk staff kindly reminded us about it—plus, a professional came to light it for us, which added such a cozy, luxurious touch. The room itself is spacious and incredibly comfortable, making it feel like a true retreat in the heart of downtown Chicago. Being just steps away from Michigan Avenue’s luxury shopping district is a major plus—everything you’d want is right outside the door, from high-end boutiques to great dining options. Public transit access is also excellent. Every staff member we interacted with went above and beyond with genuine warmth and attention to detail. It’s rare to find such exceptional service combined with elegance and convenience. I’d absolutely stay here again—and recommend it without hesitation.
Staying at Park Hyatt Chicago was an absolute delight. The room was spacious and impeccably designed, with brand-new amenities that made the experience feel luxurious and modern. The bed was incredibly comfortable—woke up feeling refreshed every morning. The bathroom was well thought out with a great shower system and smart dry-wet separation. I loved how central the location was; it's just a short walk to the train station, making downtown access super easy. There are plenty of restaurants and shops nearby, so you never run out of things to do. It’s not just about the comfort—it’s the attention to detail, the quiet elegance, and the overall vibe that makes this hotel stand out. Definitely worth every penny.
Staying at Viceroy Chicago for two nights was an absolute delight. The room size is impressive for a city hotel—spacious and well-designed, offering a comfortable retreat after a busy day of exploring. Located just steps from Michigan Avenue, everything you’d want is within walking distance: shopping, dining, and the iconic Millennium Park are literally around the corner. The nearby museums are also easy to access, making it perfect for travelers who love culture and convenience. The staff went above and beyond with warm, genuine service—always helpful and attentive without being intrusive. From the moment I arrived to the time I checked out, every detail felt thoughtfully curated. This place strikes the perfect balance between luxury, location, and comfort. Highly recommend for anyone visiting Chicago.
Staying at the Four Seasons Chicago was an absolutely wonderful experience. The location is perfect—just a short walk from downtown attractions and public transit, making it incredibly convenient for exploring the city. The room was immaculate, spacious, and offered stunning views of the skyline. The staff went above and beyond with their attention to detail and genuine hospitality. One minor note: on the night we stayed, there was quite a strong wind outside, which caused some creaking sounds from the furniture and doors. While noticeable, it didn’t detract from the overall luxury or comfort. Everything else was top-notch—from the bedding to the thoughtful amenities. This is definitely a hotel that delivers on every level, and I’d highly recommend it to anyone visiting Chicago.
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