Little Italy Hotels, Chicago

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

4679 Cheap Hotels in Little Italy - Specials, Reviews, & Last Minute Deals

Courtyard by Marriott Chicago at Medical District/UIC
3.5 star property
8.8 out of 10, Excellent, (1000)
"Very spacious room, kind staff"
United States
Jennifer
The price is AU$219
includes taxes & fees
30 Nov - 1 Dec
Courtyard by Marriott Chicago at Medical District/UIC
Eurostars Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (3079)
"Excellent stay, close to everything and the staff was super nice "
United States
Kieata
The price is AU$214
includes taxes & fees
16 Nov - 17 Nov
Eurostars Magnificent Mile
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4762)
"Great area at a good price. "
United States
Laura
The price is AU$172
includes taxes & fees
23 Nov - 24 Nov
River Hotel
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2868)
"Had a great stay!"
United States
Josh
The price is AU$193
includes taxes & fees
23 Nov - 24 Nov
Aloft Chicago Mag Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2117)
"Great stay "
United States
Melinda
The price is AU$184
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
citizenM Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (4026)
"Great place to stay. "
United States
sherry
The price is AU$204
includes taxes & fees
19 Nov - 20 Nov
citizenM Chicago Downtown
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4 out of 10, Exceptional, (2230)
"Rooms were clean with a great view of the lake and the city "
United States
Nathan
The price is AU$224
includes taxes & fees
25 Nov - 26 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2543)
"Very accessible location and amazing staff. "
United States
Fatima
The price is AU$147
includes taxes & fees
12 Nov - 13 Nov
Freehand Chicago
Hilton Chicago/Magnificent Mile Suites
3.5 star property
9.0 out of 10, Wonderful, (3201)
"Overall it was a great place to stay."
United States
Edward
The price is AU$196
includes taxes & fees
16 Nov - 17 Nov
Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9629)
"Area is great and walkable distance to touring areas. "
United States
Alejandro
The price is AU$167
includes taxes & fees
24 Nov - 25 Nov
Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very good, (4126)
"This hotel had a great location to shopping and several enjoyable restaurants."
United States
laura
The price is AU$207
includes taxes & fees
24 Nov - 25 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2271)
"Staff was wonderful, property was clean and welcoming. Great amenities for families and great location."
United States
Stephen
The price is AU$248
includes taxes & fees
24 Nov - 25 Nov
Hilton Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2686)
"Great place to stay "
United States
Larry William
The price is AU$245
includes taxes & fees
25 Nov - 26 Nov
Hotel Riu Plaza Chicago
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (295)
"Perfect location! Tons of restaurants and shopping nearby! "
United States
MaryJane
The price is AU$136
includes taxes & fees
10 Nov - 11 Nov
FOUND Hotel Chicago River North
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1004)
"Great stay"
Australia
Bart
The price is AU$180
includes taxes & fees
17 Nov - 18 Nov
Best Western River North Hotel
Crowne Plaza Chicago West Loop by IHG
3.5 star property
9.0 out of 10, Wonderful, (1635)
"Staff was friendly upon check in and the premise was very clean."
United States
Kelan
The price is AU$182
includes taxes & fees
23 Nov - 24 Nov
Crowne Plaza Chicago West Loop by IHG
Hyatt Centric The Loop Chicago
4.0 star property
9.0 out of 10, Wonderful, (2223)
"Beautiful hotel "
United States
Abigail
The price is AU$221
includes taxes & fees
23 Nov - 24 Nov
Hyatt Centric The Loop Chicago
voco Chicago Downtown - Riverwalk by IHG
3.5 star property
8.8 out of 10, Excellent, (3285)
"Great location, staff very attentive. Hotel was clean and close to riverwalk and downtown "
United States
Rocio
The price is AU$232
includes taxes & fees
26 Nov - 27 Nov
voco Chicago Downtown - Riverwalk by IHG
La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
8.6 out of 10, Excellent, (2589)
"Very nice for price and location"
United States
Deborah
The price is AU$202
includes taxes & fees
23 Nov - 24 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
Silversmith Hotel Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (2029)
"Great place to stay "
United States
Cheryl
Silversmith Hotel Chicago Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels in Little Italy with a pool

Top guest rated hotels in Little Italy

Our guide on where to stay in Little Italy

Find the best Little Italy areas for the activities you enjoy most.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Little Italy Hotel Reviews

Find out more about Little Italy

Top reasons to visit Little Italy

  • Authentic Italian Cuisine: Little Italy is renowned for its delicious Italian restaurants, offering a true taste of Italy right in Chicago.
  • Rich Cultural Heritage: Immerse yourself in the vibrant history and traditions of the Italian-American community.
  • Charming Streets: Stroll through picturesque streets lined with historic buildings and local shops.
  • Family-Friendly Activities: Enjoy a variety of attractions suitable for all ages, making it a great spot for families.
  • Welcoming Accommodations: Experience a range of charming hotels and guesthouses catering to diverse needs.

Find great hotels near Little Italy

Discover a delightful stay in Little Italy, Chicago, where a range of charming hotels and guesthouses cater to your every need. Whether you're seeking a pet-friendly retreat or a welcoming environment for the LGBTQIA community, you'll find accommodations equipped with modern amenities. Enjoy spacious rooms, relaxing lounge areas, and excellent facilities tailored for business travellers. Experience the vibrant culture and hospitality of Little Italy during your visit!

  • Congress Plaza Hotel: With a rich history and a business-centric theme, Congress Plaza Hotel is perfect for travellers seeking a productive stay near Little Italy. Located in a vibrant shopping district just 3.2km away, this 3.5-star hotel offers exceptional amenities for business guests, including multiple meeting rooms and an accessible business centre. Its classic architecture and sophisticated interiors provide a comfortable yet professional atmosphere, making it an ideal choice for those combining work and leisure.
  • Best Western Grant Park Hotel: Ideal for families, the Best Western Grant Park Hotel offers a welcoming environment with a focus on child-friendly amenities. Situated 3.2km from Little Italy, this hotel is conveniently located in a busy shopping district. Families will appreciate features such as free cribs, window guards for safety, and a first aid kit on-site. The hotel’s friendly staff ensures a comfortable stay, making it a great base for exploring the nearby attractions while providing all the necessary comforts for children.
  • Hyatt Regency Chicago: A luxurious 4-star option, Hyatt Regency Chicago combines eco-conscious practices with a vibrant city theme. Situated 3.2km from Little Italy in the heart of the city, this eco-certified hotel is perfect for business travellers and eco-friendly guests alike. It offers extensive business facilities, including a conference space and multiple meeting rooms. The hotel’s modern design and upscale amenities create a sophisticated environment, making it an excellent choice for those who appreciate both luxury and sustainability.

Where to stay near Little Italy

Little Italy in Chicago offers a delightful blend of family-friendly activities and vibrant urban charm. Stroll through its picturesque streets, enjoy authentic Italian cuisine, and soak up the friendly atmosphere. Nearby, you'll find stunning city views and inviting hotels, making it an ideal base for exploring the surrounding neighbourhoods. Experience the rich culture and history of Little Italy while discovering the scenic beauty and warmth of the local community.

  • Chicago: As a vibrant metropolis, Chicago serves as the backdrop for Little Italy. Renowned for its rich culture and diverse attractions, the city welcomes visitors year-round, with peak travel from June to August. Guests are drawn to Chicago for family outings, outdoor adventures, and city-themed experiences. Explore the bustling shopping areas, catch a game at a local stadium, or enjoy the lively entertainment venues. Chicago's landmarks, such as its iconic sports facilities and tourist precincts, promise an engaging and memorable visit.
  • Downtown Chicago: Located a mere 3.2km from Little Italy, Downtown Chicago is a dynamic neighbourhood bursting with energy. This area sees a steady influx of travellers throughout the year, particularly from July to September. Families and outdoor enthusiasts alike flock to enjoy the myriad of shopping options, theatre performances, and arena events. Proximity to notable landmarks, including stadiums and tourist precincts, enhances the experience, making Downtown Chicago an essential stop on your holiday itinerary.
  • The Loop: Also situated 3.2km from Little Italy, The Loop is a bustling neighbourhood that encapsulates the essence of city life. With visitor numbers peaking in March to April and July, this area attracts families and outdoor lovers seeking vibrant city experiences. The Loop is home to a variety of shopping districts, theatres, and entertainment facilities. Visitors can enjoy urban parks and iconic stadiums nearby, making it an exciting destination to explore while visiting Chicago.

Things to do near Little Italy

Little Italy offers a delightful blend of family-friendly activities and urban charm, making it an ideal vacation spot. Explore educational attractions, indulge in shopping, and enjoy the vibrant arena entertainment facilities nearby. With its rich cultural heritage and lively atmosphere, Little Italy invites visitors to savour authentic Italian cuisine and experience the local community spirit.

Shopping

In Little Italy, check out Maxwell Street Market, just 1.1km away, offering a vibrant mix of local goods. For a larger experience, Chicago Place Mall and 900 North Michigan Shops, both 4.8km away, provide a variety of shopping options in a lively atmosphere.

Recreation

Wrigley Field, a vibrant sports stadium 9.7km from Little Italy, offers an energetic atmosphere for sports enthusiasts. Just 3.2km away, the House of Blues Chicago invites you to enjoy live music in a lively setting. For relaxation, Northerly Island Natural Area, 4.8km away, provides a tranquil escape in nature.

Adventure

Explore the Salt Creek Trail, a scenic hiking experience located 16.1km from Little Italy, perfect for outdoor enthusiasts seeking adventure amidst nature. For family fun, visit Rainbow Falls Waterpark, situated 32.2km away, offering thrilling water attractions and entertainment for all ages.

Nightlife

The nightlife in Little Italy is vibrant and filled with cultural charm. Catch a show at the iconic Chicago Theatre or the Cadillac Palace Theatre, both offering a blend of entertainment and romance. For a unique experience, visit the historic Auditorium Building and Theatre, all within a short distance.

Booking tips and Expedia advantages for Little Italy

For a budget-friendly visit to Little Italy, Chicago, consider travelling between December and February, when accommodation prices are lower. Mondays tend to be the cheapest days to stay, while Saturdays are pricier. Use Expedia to compare hotel prices, and look for package deals that combine flights and activities to save even more. Take advantage of free activities in the area, and explore using public transport, which is an affordable way to navigate the city. By planning your trip during off-peak seasons and utilising online resources, you can enjoy a memorable stay without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Little Italy are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Little Italy is Monday. The most expensive day to stay around Little Italy is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to narrow down your options based on your budget, preferred location, and the type of accommodation you desire. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some cash by combining your Little Italy hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Little Italy

Little Italy in Chicago is perfect for families and city lovers, offering a delightful mix of urban parks, historic buildings, and skyscrapers. Explore the rich culture and family-friendly experiences that the area has to offer. Whether you're strolling through the vibrant streets or enjoying a meal at a local eatery, there's something for everyone in this charming neighbourhood.

  • McCormick Place: A premier event and conference venue, McCormick Place offers a dynamic atmosphere for business events. With its expansive exhibit halls and modern facilities, it hosts a variety of conventions and trade shows, making it a vibrant hub for networking and innovation.
  • Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a bustling street lined with upscale shops, restaurants, and iconic landmarks. Enjoy a stroll along this lively thoroughfare as you soak in the urban energy and explore the rich architectural heritage of Chicago.
  • Grant Park: Often referred to as Chicago's front yard, Grant Park is a beautiful urban oasis. Perfect for families, it features lush gardens, walking paths, and open spaces for picnics, offering a refreshing escape from the city's hustle and bustle.

Best time to go to Little Italy

The best time to visit Little Italy can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Little Italy falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Little Italy falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low

The nearest major airports for your trip to Little Italy

Accessing Little Italy in Chicago is convenient via its major airports. Chicago O'Hare International Airport (ORD) is approximately 24.1km away, with nearby hotels like Loews Chicago O'Hare Hotel and Hyatt Regency O'Hare Chicago, both within 3.2km. Midway International Airport (MDW) is about 11.3km from Little Italy, offering luxury stays at Trump International Hotel & Tower and Nobu Hotel Chicago, both roughly 12.9km away. For those considering Chicago Executive Airport (PWK), it is situated 33.8km from Little Italy, with options like Crowne Plaza Chicago-Northbrook just 1.6km away. Each airport is well-connected to these accommodations, making your travels seamless.

Frequently asked questions

What's it like in Little Italy?
Travellers to Chicago's Little Italy neighbourhood will be sure to enjoy a stay here. Are you looking for Little Italy travel tips? Make sure that you visit Credit Union 1 Arena and Jane Addams' Hull-House Museum while you're in the neighbourhood.
Where is the best place to stay in Little Italy?
Based on Expedia customer reviews, Courtyard by Marriott Chicago at Medical District/UIC is the highest ranked property in Little Italy. This hotel offers a restaurant and a fitness centre.
How many hotels are there in the Little Italy area?
Expedia has 27 hotels and other accommodation options in Little Italy to choose from, making this an ideal home base for exploring the greater Chicago area.
If I need to cancel my hotel reservation in Little Italy, will I receive a refund?
Yes, the majority of hotel room reservations are refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to review the best options available in Little Italy.
What are the top things to see and do in Little Italy?
Credit Union 1 Arena, Jane Addams' Hull-House Museum and Provision Theater are just a few attractions to check out in Little Italy. While you're out sightseeing, Michigan Avenue and United Center are a couple of additional sights to visit in Chicago.
How can I get around Little Italy and the greater Chicago area?
Looking for a quick way to explore more of the city? Catch a ride on metro transit at Racine Station and UIC-Halsted Station. To venture out of town, take a train from Chicago Halsted Station.

Explore a world of travel with Expedia