Hotels in Little Italy

Little Italy: Where Vibrant Culture Meets Urban Serenity

Nestled just south of downtown Chicago, Little Italy is a vibrant cultural enclave that pulsates with the flavours and traditions of its Italian heritage. Stroll along the charming streets, where fragrant aromas waft from family-run trattorias and bustling cafes. Key attractions include the historic University of Illinois at Chicago and the bustling Taylor Street, a culinary haven for pizza aficionados and gelato lovers alike. This neighbourhood not only offers a taste of Italy but also invites visitors to experience its rich history, festive street fairs, and warm community spirit, making it a delightful escape in the heart of Chicago.

Things to do near Little Italy

Little Italy is a vibrant urban enclave where charming streets brim with life and a rich cultural tapestry unfolds. Visitors can indulge in delightful culinary experiences, explore eclectic boutiques, and soak up the lively atmosphere in parks. With opportunities for leisurely strolls, spirited performances, and recreational activities, this area is a must-visit for anyone seeking a taste of authentic culture and community.

• Lakefront TrailOpens in a new window – Step out for a refreshing stroll or bike ride along the Lakefront Trail, an urban park that hugs the shores of Lake Michigan. This scenic route offers stunning views of the water, making it an ideal spot for exercise or a leisurely outing. Along the way, you'll find lush greenery and various recreational facilities that cater to sports enthusiasts and families alike.
• Armitage AvenueOpens in a new window – Discover the charm of Armitage Avenue, a vibrant street lined with unique shops, cafes, and eateries. Take your time to explore the various boutiques and indulge in delicious bites from local restaurants. It's a perfect place to soak up the local vibe and enjoy a leisurely afternoon.
• Chicago RiverwalkOpens in a new window – Head to the Chicago Riverwalk, a bustling tourist precinct where you can relax by the water, enjoy a meal at one of the many riverside cafes, or simply watch the world go by. With its beautiful views and lively atmosphere, it’s a great spot to connect with the city.
• Oak Street BeachOpens in a new window – Spend a sunny day at Oak Street Beach, where you can unwind on the sandy shores or dip your toes in the refreshing waters of Lake Michigan. This popular beach is perfect for sunbathing, picnicking, or taking a scenic walk along the shoreline.
• State StreetOpens in a new window – Experience the hustle and bustle of State Street, a major thoroughfare known for its shopping and entertainment options. Browse through a mix of department stores and local shops, and enjoy the vibrant street life as you take in the sights and sounds of this iconic location.

4 tips for savvy savings when booking a hotel in Little Italy

1. Book for the cheapest times: The most cost-effective time to visit Little Italy is during January, February, and December, when hotel prices are generally lower. An ideal stay would be at least 2 to 3 days to fully appreciate the area's notable landmarks and cultural offerings. Visitors can explore a variety of attractions, including historic sites, such as the modern lighthouse and ancient ruins, as well as engaging in activities at the natural history museum and various parks. This budget-friendly trip promises great value for money, allowing you to soak in the rich history and vibrant culture without breaking the bank.
2. Look for last-minute deals on Hotels.com: To explore last-minute deals to Little Italy on Hotels.com, you may begin by checking the DealsOpens in a new window or Last-Minute Deals section, where you're more likely to see discounted hotel rates as your travel date approaches. To stay updated on flash sales and exclusive last-minute offers, consider enabling email alerts or push notifications from Hotels.com. Additionally, the Smart Shopping feature in the app allows you to compare hotel prices and amenities, helping you secure the best options available. With these tools, you'll be informed about price drops or room availability, making it easier to plan a spontaneous getaway.
3. Be flexible with dates: Prices may fluctuate based on various factors, including the hotel's location, star rating, and the time of year, so being flexible with your travel dates could help you save on your stay in a hotel in Little Italy. For those seeking distinctive accommodations, boutique hotels often provide a more personalised experience and may offer better value. When you book through Hotels.com, we will inform you if the price for your chosen dates is above or below the average. If the price is on the higher side, we’ll suggest more affordable dates, which could help you secure a better deal.
4. Consider your location: Choosing to stay near key attractions or city centres may offer convenience, but it often comes with higher expenses. For more affordable options, you might consider hotels located in less central areas or neighbourhoods, striking a balance between cost and accessibility to the places you intend to visit. Independent hotels situated a bit further out are usually more likely to be affordable and can provide a more authentic experience.

Best time to go to Little Italy

Little Italy has a varied climate due to its size, so the best time to visit depends on the region and your preferences for weather and crowds. If you’re looking to soak up the lively atmosphere in Little Italy, June to August are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, with light rainfall. However, if you prefer a more relaxed experience, January, February, and April are perfect for a quieter getaway, marked by light rainfall and mostly sunny to mostly cloudy conditions.