Work With Inteletravel To Plan The Perfect Chicago Vacation
While there is plenty to do and see throughout the Windy City, arranging your itinerary and finding and booking the many different aspects of your trip yourself shouldnt be one of them!
InteleTravel Advisors are available to help you navigate any hurdles and create the best trip featuring your personal preferences.
Our team of qualified travel professionals will work with you to create a custom itinerary so you can see and experience everything you want during your visit, while securing valuable upgrades to further enhance your vacation experience!
The Best Boutique Hotels In Chicago
Treat yourself to a stay in one of the most special and unique hotels in Chicago
While massive hotel chains aren’t for everyone, Chicago boasts some of the best hotels, which you should totally check out. Thankfully, the Windy City has an impressive assortment of boutique properties that trade size for warm, personalized service and a huge helping of character. And these are things we certainly look for in our hotels here at Time Out.
Whether it’s your first time here or you’re planning a cheeky staycation, these boutique hotels make a cozy backdrop when you’re away from home. Our top picks range from a stylish stunner in Wicker Park to a British import crowned by one of the citys best rooftop pools. With choices like these, you’ll be packing your bags in no time. Happy vacations, people. Or maybe even a staycation? Because any excuse to stay in some of these…
RECOMMENDED: Find more places to stay with our guide to the best downtown Chicago hotels in the Loop. Or stay one of the coziest Airbnbs near Chicago this winter. Feeling fancy? Check out the most lavish Airbnbs in Chicago. Feeling quieky? Here’s the most unique Chicago Airbnbs.
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Is It Safe To Stay In Downtown Chicago
Generally speaking, Downtown Chicago/The Loop is a safe place to stay. There are pickpockets, but you should be fine as long as youre vigilant about your belongings and surroundings. It may also be a good idea to leave valuables in your Chicago hotel room while out and about.
Thanks for reading my guide to where to stay in Chicago I hope it helps you pick the best neighborhood and area for you. And dont forget to check out our list of the 33 best things to do in Chicago for more great vacation inspiration.
The Windy City is sure to be wonderfully memorable regardless of where you stay have fun!
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The Westin Chicago River North
Located in downtown Chicago, The Westin Chicago River North sits on the Riverwalk near Clark/Lake subway station.
Besides popular attractions and fine shops, the hotel is also not far from Michigan Avenue.
Experience the amazing stay from different options of Traditional Rooms and Luxury Suites with stunning views.
Each unit has a flat-screen TV, a seating area, a coffee maker, and a marble bathroom.
Try complimentary one-on-one and group training sessions or work out on your own with plenty of equipment at its onsite gym.
Relax by the Chicago River and indulge in delightful menus at 320 RiverBar.
For dinner, make your way to Kamehachi Sushi Bar and enjoy a variety of nigiri, maki, and more.
- Guest Rating: 9.0
Chicago Hotels: Front Row Seat To Lakeside Beauty
The beauty of Lake Michigan, along with sights like Navy Pier, Millennial and Grant Park, the shopping areas of Magnificent Mile, and the historic mansions of Chicagos Gold Coast neighborhood offer jaw-dropping city vistas that demand to be seen from above. Grab your chance, by choosing to stay at one of these awesome hotels.
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Where To Stay In Chicago: Best Areas And Hotels
Chicago is the best. The largest city in Illinois is one of the most exciting cities in the United States. It has a skyline that would turn most cities green with envy and has vibrant city life and culture. Chicago is also situated on the shores of Lake Michigan and even has waterfront and watersport activities on offer.
Of course, as the third most populated city in the United States, it is no wonder that the windy city is full of things to do and places to eat. The massive city has lots of different neighborhoods with different qualities. This guide will cover where to stay in Chicago and which areas you should choose.
Well introduce you to each of Chicagos best areas. From the citys trendiest neighborhoods to its most convenient, lets delve into where to stay in Chicago.
Palmer House A Hilton Hotel
17 East Monroe Street
One Of The Coolest Top Hotels With A View in Chicago
Featuring a hairdresser, a health club and an indoor swimming pool, Palmer House A Hilton Hotel is located in Chicago Loop district, 1 km from Millennium Public Park. Situated in the centre of Chicago, the venue gives quick access to Macy’s on State Street.
The – art Shedd Indoor Aquarium is less than 2.4 km away. The accommodation is also next door to CIBC Theatre, and near a railway station. London Guarantee Building is just a few minutes’ drive away.
- Free Wi-Fi in public areas
- Luggage storage
If Youre Looking For A Great Hotels With A View In Chicago Downtown, Check Out Millennium Knickerbocker Chicago
About 900 metres from the Oak Magnificent Mile Street, the 4-star Millennium Knickerbocker Chicago Hotel offers an a la carte restaurant on site. The venue is set in Magnificent Mile district, within easy reach of the skyscraper 360 Chicago Observation Deck.
Chicago Water Tower is located near the accommodation, and Midway International airport is approximately a 25-minute drive away. London Guarantee Building is 15 minutes’ walk from the hotel. This stylish property is within a short driving distance of The Art Institute of Chicago.
- Luggage storage
This Budget Friendly Hotels With A View In Chicago Offers All You Need For The Ultimate Vacation
- Free Wi-Fi in rooms
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Bucktown & Wicker Park
Known for its indie-artist vibes, entrepreneurial spirit, and buzzing six corners intersection, the Bucktown-Wicker Park neighborhood stands as one of Chicagos hippest destinations. Milwaukee and North Avenues are go-tos for resale and record shopping alongside other eclectic finds , while Damen Avenue and Division Street abound with upscale boutiques and award-winning restaurants.
Where to stay: The Robey is a favorite for its industrial-chic design and prized location . Check in, then check out any of the propertys common areas, including Cabana Club and Up Room, and two rooftop options for those seeking a little sun with their stay. Come morning, scope out brunch at Café Robey, a quaint corner eatery with a knack for American comfort fare e.g. Duck Hash, house made Biscuits and Gravy, and Chili Butter Shrimp and Grits.
Things to do: Get some fresh air along the 606, a 2.7-mile elevated rail trail that takes the cake as the longest greenway initiative of a former rail line in the country. Upon your descent at Milwaukee Avenue, swing into Ipsento 606 for some cold brew and tiny doughnuts , then stroll the shops of Damen Avenue, including the recently opened PRERY Collective, a boutique collaboration between local style curators Sararose Krenger and Emily McKenney.
Things To See In River North
River North covers the distance from the Chicago River to Chicago Avenue and the Magnificent Mile. It is near the city center and downtown neighborhoods but also has a strong sense of its own identity. River North was once an industrial area and has been slowly gentrified over the past century.
When you arent browsing River Norths art galleries or sipping cocktails, it is worth walking the Magnificent Mile. The Magnificent Mile is actually called North Michigan Avenue. But the street coined its name due to the many prominent cultural attractions and venues lining its sidewalks. You can window shop, drop into fun attractions like The Dr. Seuss Experience or The Office Experience, or book a table at one of the fine dining restaurants. Walking the Magnificent Mile is an excellent way to spend an afternoon if you want to be spontaneous but be guaranteed a lot of entertainment and hospitality options.
Overall, River North is a fun, stylish place to stay in Chicago. If you are wondering where to stay in Chicago for a socialite experience, River North is your best choice. The neighborhood ticks the boxes for food, drink, and culture. Plus, you can still find waterfront views thanks to its positioning along the Chicago River.
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Budget Hotels In Downtown Chicago
If you are looking to where to stay in Chicago near the Magnificent Mile, here are a few budget-friendly recommendations:
Address: 166 E Superior St, Chicago, IL 60611, United States
There are 216 total rooms and suites in the Magnificent Mile Collection of the Chicago Hotel Collection. This hotel is located just a few blocks from Chicagos famous Michigan Avenue and Lincoln Park. It is one of the best hotels to stay in Chicago to be close to its most known attractions.
Address: 323 E Wacker Dr, Chicago, IL 60601, United States
Swissotel Chicago is within a 10-minute walk away from the waters edge, located in the heart of downtown, just steps from the Magnificent Miles finest boutiques, restaurants, and nightlife this glass-and-steel triangle hotel offers a unique perspective of the city.
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Best Hotels In Chicago Streeterville
Luxury: Four Seasons Chicago
The Four Seasons hotels are consistently ranked amongst the best hostels, and the Four Seasons Chicago is not one to break this pattern. Each room features marble bathrooms, a guest spa with a fifty-meter indoor pool, and an award-winning restaurant on-site. You can choose from a range of suite and room options, all of which will put luxury into your stay in Chicago. Book it on TripAdvisor / Booking.com
Mid-range Loews Chicago Hotel
Loews Chicago Hotel is chic. The hotels newly renovated interior features an indoor pool, 24-hour fitness center, and business meeting rooms. Loews Chicago Hotel is also excellently located for city and lake views. It is only a short walk from Navy Pier and Ohio Street Beach. Compare on TripAdvisor / Booking.com
Budget: St. Clair Hotel / Freehand Hotel
Budget-friendly accommodation just isnt in Streetervilles vocabulary. The cheapest option is St. Clair Hotel, where the rooms start at around $300 per night. The European-style hotel is brilliantly located right next to Magnificent Mile and has beautiful, spacious rooms. Compare on TripAdvisor / Booking.com
However, you may wish to look at accommodation in River North or in Downtown Chicago along the Chicago River instead. These areas have more budget options and are within walking distance of Streeterville. See it on TripAdvisor / Booking.com
VRBO: Two-bedroom apartment
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Best Hostel In Streeterville: Freehand Chicago
Set in stunning Streeterville is Freehand Chicago my top pick for where to stay in Streeterville. This charming hostel is built in a classic 1920s building and comes complete with stylish décor. It has a cocktail bar, a fitness center, and laundry facilities on-site. The location is a perfect base to explore the city, and you can expect lockers and towels to be provided.
Ultimate Luxury Hotels With Views In Chicago
Youll be impressed with this next set of 5-star hotels. Chicagos ultimate luxury hotels with views will cost you over $400 per night. Its worth it because these are the most fancy hotels in Chicago & the most romantic hotels in Chicago.
|Triple AAA Diamond award winning restaurant|
Including the best hotels in Chicago downtown neighborhoods like Streeterville, River North, and Fulton Market. These are the top-tier Chicago hotels downtown with views of the surrounding cityscape and Lake Michigan. Read on to discover the ultimate luxury hotels. Chicago vacations dont get much better than this!
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Chicago Loop Where To Stay In Chicago For First
Chicago Loop is the best area to stay in Chicago for first-time travelers because it is the most central area of Chicago downtown. If you stay here, you will be located in the middle of everything, within walking distance to Chicagos top tourist attractions, as well as many restaurants, bars, and shops.
Some of Chicagoâs most iconic buildings and skyscrapers are located here, including Willis Tower and the Marquette Building. The Willis Tower in the west of the neighborhood offers panoramic views across the city from its 103rd story viewing platform.
Willis Tower is surrounded by other notable buildings within easy walking distance. The Rookery Building and the Federal Reserve Bank of Chicago are both just around the corner.
One of the best areas to stay in the Loop is around Michigan Avenue. The avenue stretches right through the city center and is lined with top attractions, plentiful shopping streets, and excellent dining venues.
Michigan Avenue sits right between the bustling Theatre District and the beautiful Grant Park. Staying here will have you perfectly placed to explore the best the city has to offer, entirely at your convenience.
If you love art, you will love this location. Michigan Avenue is surrounded not only by some of Chicagoâs top art galleries and art institutes but also some of the best areas to spot street art.
The Loop has plenty of accommodation options that suit all budgets, from backpacker hostels to luxury hotels.
Things To Do In Streeterville
Apart from Magnificent Mile, another massive draw of Streeterville is its waterfront. The entire east side of the neighborhood is on the shores of Lake Michigan. Streeterville has Ohio Street Beach in the south, which is connected to Oak Street Beach in the north by a pretty lakeside footpath. There is plenty of quiet green space to sunbathe, jog, and picnic.
Navy Pier is also located along Streetervilles Lake Michigan shores. Once a navy training center, the pier is now a permanent fairground with rides and Chicagos funhouse maze. There is also the Chicago Childrens Museum and even Chicago Shakespeare Theater, an ideal venue for some entertainment.
If you are undecided between River North and Streeterville, whether you would prefer to be just within walking distance from the shores of Lake Michigan is the best decider. Both River North and Streeterville have great bars, shops, and culture, so Lake Michigan is the only significant difference.
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Things To Do When You Stay In Downtown Chicago
If you want a quiet space in the Chicago Downtown neighborhood, Grant Park is never too far away. The 319-acre park separates the busy streets from Lake Michigan, and you can relax and wander the park to admire views of the water and cityscape skyline. For taking pictures, Millennium Park has the best skyline view of Chicago Downtown.
On a warm day, the parks 12th Street Beach is the best place to sunbathe. And, on a rainy day, Grant Park has the lakefront Museum Campus. The Museum Campus is a 57-acre area containing the Field Museum, Adler Planetarium, and Shedd Aquarium, which will keep you well-occupied indoors.
The main attractions in the urban side of Downtown Chicago are Skydeck Chicago and the Museum of Contemporary Art. There is also McCormick Place Convention Center which has lots of events. However, South Loop is also one of the best areas to stay in Chicago just to explore the streets and soak up the atmosphere.
Everything is within walking distance and easy access. If you are only visiting for a few days or if you are visiting for the first time, Downtown is where to stay in Chicago.
Best Hotels In Downtown Chicago
Luxury: Pendry Hotel
Pendry Hotel is inner city class. The hotel is set in an industrial-looking high rise, right at the intersection of Michigan Avenue and Wacker Place. It is one of the best hotels to stay in Chicago if you want luxury facilities. Pendry Hotel has a fitness suite, business center, restaurant, and terrace. See rates, reviews and availability on TripAdvisor / Booking.com
Mid-range: Hotel Blake
Hotel Blake is a boutique hotel situated between Grant and Millennium Park. Like Pendry Hotel, Hotel Blake has an old-money class. But the prices are slightly lower than those at Pendry Hotel, so perfect if you have a mid-range budget in mind.
It has a fantastic location and is just a ten-minute walk from the Chicago Art Institute. Hotel Blake has a fitness center, restaurant, 24-hour business center, and free wifi. Compare rates and availability on TripAdvisor / Booking
Budget: HI Chicago Hostel
Finding a budget place to stay in Chicago can be challenging, especially downtown. HI Chicago Hostel is an excellent option if you can get a space this hostel is always in demand. HI Chicago Hostel has a games room, lounge, and 24-hour reception. You can choose a private or dorm room, too. Compare Rates and Availability on TripAdvisor / Booking
VRBO: Stylish two-bedroom apartment
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Streeterville Is The Place To Stay In Chicago For Shopping
Streeterville is one of the smaller Chicago neighborhoods and is found northwest of the Loop. You will find the Navy Pier to the west and the Magnificant Mile to the east.
The Magnificant Mile is a portion of Michigan Avenue known for having some of the best shopping in the country!
You will find a number of high-end stores and boutiques here perfect for a shopping spree.
Burberry, Louis Vuitton, Nike, Nordstrom, and more have stores here.
When you are done shopping, you can check out museums such as the Chicago Childrens Museum and Museum Of Contemporary Art Chicago.