Hotels in Uptown

Skyline Serenity: Embrace the Allure of Uptown’s Lakeside Wonders

Discover Uptown, Chicago, a vibrant neighborhood where eclectic culture meets stunning lakefront views. Known for its historic architecture and lively arts scene, Uptown offers charming theaters like the Aragon Ballroom, perfect for music lovers. Stroll along Montrose Beach for sun-soaked relaxation or explore the diverse culinary offerings that reflect the area's heritage. With its unique blend of urban energy and serene lakeside escapes, Uptown is a captivating hideaway that showcases the best of Chicago's rich tapestry. Experience the magic of this off-the-beaten-path gem, where every visit promises new adventures! For the best hotel rates in Uptown and to enhance your stay, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Where to stay in Uptown

Uptown, Chicago, offers vibrant attractions like Wrigley Field, Michigan Avenue, and Navy Pier. Wrigley Field is a must for sports enthusiasts, while Michigan Avenue is perfect for shopping and dining. Navy Pier provides entertainment and stunning lake views. For accommodations, expect a range from budget-friendly hotels to luxury options, with varying rates. First-time visitors will find Michigan Avenue the most appealing, thanks to its central location and numerous attractions. Enjoy your stay in this lively neighborhood! Here are some of our travelers' favorite hotels in Uptown:

1. Near Wrigley FieldOpens in a new window: This vibrant area is perfect for sports enthusiasts and families, offering close proximity to the famous Wrigley Field. It boasts a lively atmosphere with plenty of dining and entertainment options. For accommodations, consider Hotel Zachary Chicago, a Tribute Portfolio HotelOpens in a new window, a 4.0-star hotel that caters to business travelers with multiple meeting rooms and an accessible business center. Another option is The Chicago Hotel Collection - WrigleyvilleOpens in a new window, a 3.5-star hotel that welcomes pets, making it a great choice for travelers with furry companions. For families and adventure seekers, Chicago Guest House WrigleyvilleOpens in a new window is also a 4.0-star hotel offering various recreational activities nearby, including ice skating, sailing, and hiking, along with amenities tailored for children.
2. Near Michigan AvenueOpens in a new window: This bustling area is a shopper’s paradise, known for its iconic Magnificent Mile and vibrant city life. It’s ideal for both business and family travelers. Comfort Inn Matteson - ChicagoOpens in a new window is a 2.5-star hotel that offers essential business amenities and family-friendly services, including free cribs for little ones. Presidential Inn & SuitesOpens in a new window, also a 2.5-star motel, provides entertainment options like LED TVs and cable, perfect for relaxing after a day of exploring. Lastly, Staybridge Suites Schererville, an IHG HotelOpens in a new window is a 3.0-star hotel allowing pets, making it suitable for pet owners looking to enjoy the city without leaving their companions behind.

What to do in Uptown

A visit to Uptown offers three days of vibrant experiences amid stunning lakes, lush parks, and striking skyscrapers. Enjoy activities like boating, birdwatching, and hiking, along with a lively arts scene featuring theater, live music, and opera. It's a perfect blend of nature and culture for every traveler. Here's a quick itinerary to make the most of your trip to Uptown:

• Day 1: Begin your adventure on Michigan Avenue, also known as the Magnificent Mile, where you can shop at a variety of high-end stores and boutiques. After indulging in some retail therapy, take a moment to visit the Holy Name Cathedral, an architectural gem that offers a serene atmosphere for reflection. Wrap up your day at Water Tower Place, where you can enjoy dining options or catch a show at the nearby theaters, all while soaking in the vibrant city life.
• Day 2: Start your day at Navy Pier, where you can explore the attractions, enjoy views of Lake Michigan, and grab a bite at one of the many eateries. Next, take a short walk to Tribune Tower, an iconic building rich in history and stunning architecture. Conclude your day with a relaxing time at Ohio Street Beach, where you can unwind on the sandy shores, enjoy the skyline views, and perhaps dip your toes in the water.
• Day 3: Kick off at Millennium Park, a cultural hub where you can admire the famous Cloud Gate sculpture, commonly known as The Bean. Then, take a leisurely stroll through Grant Park, often referred to as Chicago's front yard, featuring beautiful gardens and art installations. Finish your day at the Chicago Riverwalk, where you can enjoy a scenic walk along the river, dine at waterfront restaurants, or simply relax and take in the stunning views of the cityscape.

5 tips to find a great Uptown hotel deal

1. Book for the cheapest times: The most budget-friendly time to visit Uptown is during January, February, and December, when hotel prices are more affordable. To fully experience the area’s highlights, it’s recommended to stay for at least 2-3 days. While you’re there, be sure to explore the beautiful lake and iconic skyscrapers that showcase the area's stunning architecture, making your trip a great value for money.
2. Look for last-minute deals on Hotels.com: If you're looking for last-minute hotel deals in Uptown, Hotels.com is a great place to start. Head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section, where you could find discounted rates on hotels as your travel date approaches. Prices can vary, so keep an eye out for the best value options. To ensure you don’t miss any opportunities, consider enabling email alerts or push notifications for flash sales and special promotions. For any questions or to check availability, visiting the site regularly is always a good idea.
3. Be flexible with dates: Hotel prices can fluctuate due to factors like the location, star rating, and the season. As a result, being flexible with your travel dates may help you save on hotel expenses in Uptown.
4. Consider your location: When booking on Hotels.com for your vacation, think about your location. Staying near major attractions or city centers can offer convenience, but it usually tends to be more expensive. For more affordable options, consider hotels in less central areas or neighborhoods, striking a balance between cost and easy access to the places you want to visit.
5. Upgrade with One Key: Book your next stay in Uptown and join Hotels.com’s One Key programme which allows members to earn and redeem rewards points for hotel bookings. Move through blue, silver, gold and platinum tiers and unlock benefits such as earning free nights, room upgrades, special discounts, and exclusive deals for members. Sign up now.

What to eat in Uptown

Here are a few popular dishes in Uptown, Chicago, Illinois, United States of America:

• Chicago-style Hot Dog: A quintessential Chicago experience, this all-beef frankfurter is served on a poppy seed bun and topped with a vibrant mix of yellow mustard, chopped onions, sweet relish, tomato slices, a pickle spear, and sport peppers. The unique combination of flavors and textures showcases the city’s culinary creativity, and it's often enjoyed at local street vendors or iconic eateries.
• Italian Beef Sandwich: This savory sandwich features thinly sliced, seasoned roast beef simmered in a flavorful broth, served on a crusty Italian roll. It's typically topped with giardiniera or sweet peppers, making every bite a delicious experience. Perfect for a quick meal, this dish reflects the rich Italian heritage of Chicago, often enjoyed during lunch breaks or casual gatherings.

Best time to go to Uptown

Uptown experiences its lowest average temperature in January, at 25.7°F (-3.5°C), while July is the hottest month, with an average temperature of 73.4°F (23.0°C). June is typically the wettest month. If you’re looking to soak up the lively atmosphere in Uptown, June, July, and September are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, accompanied by light rainfall. However, if you prefer a more relaxed experience, January, November, and December are perfect for a quieter getaway, marked by light rainfall and mostly sunny to mostly cloudy conditions.