Hotels in Little Italy

Discover Little Italy: Where Heritage Meets Vibrant Urban Life

Little Italy in Chicago is a vibrant cultural enclave that celebrates its rich Italian heritage through charming streets lined with authentic trattorias and lively cafés. Nestled near the University of Illinois, this historic neighbourhood invites you to savour delicious pasta and gelato while exploring cultural landmarks like the Italian Cultural Center. The area’s picturesque urban parks offer a delightful escape, perfect for a romantic stroll. With its lively atmosphere and a sense of community, Little Italy promises an unforgettable experience steeped in history, flavour, and warmth—ideal for food lovers and culture seekers alike. For our best hotel rates in Little Italy and to enhance your stay, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Top locations to stay in Little Italy

Little Italy, Chicago, is a vibrant area rich in culture and cuisine. Nearby, Michigan Avenue is renowned for its shopping and architecture; Grant Park offers lush green space and events; while Willis Tower provides breathtaking city views. Accommodation in these areas ranges from luxurious hotels to charming boutique stays, catering to various budgets. For first-time visitors, Michigan Avenue is ideal due to its central location and access to key attractions, making it a perfect base for exploring the city. Here are some of our travelers' favorite hotels in Little Italy:

1. Near Michigan AvenueOpens in a new window: This vibrant area is perfect for those looking to immerse themselves in Chicago's shopping and business culture, with its proximity to high-end retailers and corporate offices. The selection of hotels caters to various traveller affinities, from adventure seekers to business professionals. Consider staying at Chicago Marriott Downtown Magnificent MileOpens in a new window, a 4-star hotel that offers excellent business amenities, including a 24-hour business centre and multiple meeting rooms, making it ideal for corporate travellers. Another option is InterContinental Chicago Magnificent Mile by IHGOpens in a new window, a 4.5-star hotel steeped in history, featuring family-friendly services and located in a national historic building. Lastly, The GwenOpens in a new window, a luxury 4.5-star hotel, welcomes pets and has extensive business facilities, catering to both leisure and business guests.
2. Near Grant ParkOpens in a new window: This family-friendly locale is known for its outdoor spaces and cultural attractions, making it a great base for exploring the city. The area is filled with hotels that provide amenities geared towards families and business travellers alike. Hotel BnBOpens in a new window is a budget-friendly 2.5-star hotel offering entertainment options like flatscreen TVs, perfect for families. For a more upscale experience, Marriott Marquis ChicagoOpens in a new window is a 4-star hotel that boasts direct beach access and comprehensive business facilities. The Wheeler MansionOpens in a new window, a boutique 4-star hotel, offers uniquely designed rooms and childcare services, ensuring both comfort and convenience for families.
3. Near Willis TowerOpens in a new window: This bustling area is ideal for those wanting to experience Chicago's energetic urban vibe and enjoy shopping and dining options. The hotels here cater to business and city explorers alike. Courtyard by Marriott Chicago at Medical District/UICOpens in a new window is a 3.5-star hotel focused on business travellers, featuring a 24-hour business centre and multiple meeting rooms. For those travelling with pets, Hotel Chicago West LoopOpens in a new window is a 2.5-star hotel that allows pets and includes essential business amenities, making it a practical choice for city dwellers.

Things to do in Little Italy for first times

Three days in Little Italy offers a delightful blend of cultural experiences and recreational activities. Wander through vibrant parks, enjoy waterfront activities, and explore local shops. With opportunities for theatre, arena entertainment, and education, this charming neighbourhood provides a captivating escape for travellers seeking both leisure and cultural enrichment. Here's a quick itinerary to make the most of your trip to Little Italy:

• Day 1: Start your adventure in Chicago with a stroll along Michigan Avenue, where you can explore the iconic Magnificent Mile filled with shops and eateries. Next, visit the Aon Center, one of the tallest buildings in the city, offering stunning views from its observation deck. After that, take a leisurely walk along the Chicago Riverwalk, a picturesque waterfront space perfect for enjoying the scenery and grabbing a bite from one of the many cafes.
• Day 2: Begin your day at Grant Park, known as Chicago’s front yard, featuring beautiful gardens and monuments. After soaking in the greenery, make your way to the Harold Washington Library Center, an architectural marvel where you can explore its vast collection. Conclude your day at the Art Institute of Chicago, home to an impressive array of artworks, including pieces by Monet and Grant Wood, making it a must-visit for art enthusiasts.
• Day 3: Kick off your day at Millennium Park, where you can marvel at the Cloud Gate sculpture and enjoy the vibrant atmosphere. Following that, head over to the Field Museum of Natural History, where fascinating exhibits, including Sue the T. rex, await. Wrap up your exploration with a visit to Willis Tower, where the Skydeck offers breathtaking views of the city skyline, a perfect way to end your Chicago experience.

4 tips to find a great Little Italy hotel deal

1. Book for the cheapest times: The most budget-friendly time to visit Little Italy is during January, February, and December when hotel rates are at their lowest. Domestic travellers should aim to book their flights at least 2 months in advance for the best deals, while international travellers are advised to book at least 3 months ahead for more affordable options. Spending at least 2-3 days is recommended to fully enjoy the great value for money that this area offers, with key attractions such as a historic university, vibrant urban parks, and a cultural centre waiting to be explored.
2. Look for last-minute deals on Hotels.com: If you're looking for a spontaneous getaway to Little Italy, exploring last-minute deals can be a great way to save. To find these offers on Hotels.com, head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section, where you could find discounted rates on nearby hotels as your travel date approaches. Additionally, consider enabling email alerts or push notifications from Hotels.com to stay informed about flash sales and exclusive last-minute promotions, helping you to seize any savings opportunities that arise.
3. Be flexible with dates: Prices may fluctuate depending on factors like the hotel's location, star rating, and the time of year. Consequently, being flexible with your travel dates could increase the likelihood that you’ll save on hotel expenses in Little Italy.
4. Consider your location: When planning your holiday on Hotels.com, take your location into account. Staying nearer to major attractions or city centres may offer convenience, but it often tends to come at a higher price. For more affordable options, consider hotels in less central areas or neighbourhoods, striking a balance between cost and ease of access to the sites you wish to visit.

Best time to go to Little Italy

Little Italy 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 usually the wettest month. July to September are the peak travel months in Little Italy, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, with light rainfall. On the other hand, January, February, and April tend to be quieter times to visit, marked by light rainfall and mostly sunny to mostly cloudy conditions.