Best Places to Stay in Chicago, Illinois – Our Guide on Where to Stay in Chicago

Chicago hotels are among the most expensive in the United States at around $200 a night, and the average cost won’t change any time soon because the city’s hotels are near capacity all year round. The third-largest city in the United States is the second-most visited metropolis in the country, due in large part to its central location in the U.S., Chicago’s iconic status as one of the great American cities, the myriad of summer festivals and yearly conventions, and conferences, and sporting events that bring large crowds to all parts of the city.

Best Places to Stay in Chicago, Illinois

There is no shortage of cheap airline tickets to get to Chicago, but the real estate will set you back unless you head for a hotel outside of downtown, rent a room or house from a local, or stay in a hostel. With Our Guide on Where to Stay in Chicago, we provide all of the details on every type of accommodation you will find in Chicago. Furthermore, while you will no doubt see familiar chain hotels, we look beyond those places to find the best places for your money that might not be associated with a well-known name. Our Best Places to Stay in Chicago, Illinois consisting of mostly independent places that are unique and interesting, while providing the best deal for your dollar, whether they are expensive or moderately priced.

Chicago Districts and Layout

Chicago districts map
Click To Enlarge – Integrated Chicago districts map by Peter Fitzgerald on CC1.0

Chicago has a pretty strange layout. It is so remarkably simple in its design it almost makes no sense. It all begins with the Loop. This is the Downtown and central district of the City. Downtown Chicago was more frequently called the Loop because the eight-block area is outlined by the L train rails on all sides. the name has stuck evermore until no one really thinks why it’s the loop …it just is.

Serving as the center point most other districts are named by their distance and direction from the loop. So New North, Near West, Near South, Far North, Far West, and Far South. There is not East as, well that’s Lake Michigan. As we said it’s devilishly simple! There are several exceptions to this rule and many subdivisions within these districts.

Many of the areas are not particularly favorable to tourists so below we look at the areas you should be looking to for your trip to Chicago.

Best Areas to Stay in Chicago, Illinois

The Loop

Obviously being right in the center of things is the obvious choice, but in some cities, the center or downtown district is not the best place to be, However in Chicago it is pretty much the heart of the city and definitely one of the most popular spots with the most choice and a large number of chain hotels operating here. It’s not the best location for restaurants and things to see and do, as it’s mainly a business area, but it’s close by to all the areas that are more tourist orientated.

Magnificent Mile

Just north of the Loop is what is known as the Magnificent Mile. This is Chicago’s main shopping street and is lined with high-end luxury shops, restaurants, and night spots. Being right next to the loop, it is very central and is one of the most happening districts in the City. Upmarket Boutique hotels are the order of the day here.

River North

To the West of the Miricle Mile is River North. This is the Party District where people come to be seen. There are plenty of hotel options from budget to high-end luxury. Being right next to the Magnificent Mile and the Loop it is very well placed too. A great place to bag a bargain that is still right in the heart of it.

Gold Coast

This is an upmarket residential area but it’s got a quieter more relaxed vibe than the hustle of the downtown areas. we are heading away from the center now and you will need to travel for most things but there are plenty of eateries and the coastal setting feels a million miles away from the Metropolis you expect from Chicago.

Lincoln Park / Old Town

This is furthest away from the Loop as we get on our list. Obviously, we don’t recommend you stay in the park, like a hobo, but the built-up area behind it is still called Lincoln Park. Accommodation prices drop a little here as you are getting further away from it all, but it’s actually a great place to stay and grab a bargain.

Where ever you choose to Stay you will need to get around town, Find out how in our Getting Around Chicago Guide.

Rent a Vacation Home or Apartment in Chicago

Many people in Chicago rent their apartment or home, or a room in it, and Airbnb and VRBO are your best bets for finding a safe and accommodating place to stay on your trip to Chicago. For those of you unfamiliar with Chicago and its suburbs, stick to the neighborhoods mentioned in this article when looking at homes, apartments, and rooms for rent, so that you do not find yourself in a desperate part of town or in a nice neighborhood, miles and miles from the action. In a quick search, we found rooms in nice Chicago apartments and houses for $50-$150 a night, entire lofts, studio apartments, and middle-class homes for $155-$300 a night, and mansions in the Gold Coast for $3,000-$5,500.

Stay at a Bed & Breakfast in Chicago – Something a little different.

Chicago has a huge B&B scene, and The Chicago Bed and Breakfast Association does a great job of listing B&B locations that provide great accommodations and service. Check them out at We found a spot at The Monastery of the Holy Cross Bed and Breakfast, and while it is owned by the monastery, it feels like Grandma’s place, if your grandmother is into crucifixes and older furniture.

At The Monastery, there is an upstairs loft apartment that has three bedrooms and a downstairs garden apartment with two bedrooms. The cost is around $200 a night for two people to rent either of the apartments and after two people, each additional adult is $50 and each additional child is $30. And the kicker? Monks bring you food in the morning if you stay in the loft apartment, and you do truly feel blessed by their presence and food offerings of French toast, eggs, hash browns, muffins, and fruit. The garden apartment, on the other hand, has a fridge stocked with goodies that you can prepare for yourself in the provided kitchen.

Find a Great Hotel in Chicago – Our Top Ten List of Chicago Hotels

The neighborhoods we include in our listings are the safe ones that are in Downtown Chicago, or close to it. We provide a brief rundown of the neighborhood, along with our best picks for accommodations there, attempting to stay clear of the massive chain hotels that you will find around the city, which aren’t bad, but they already have a well-known reputation.

Great Hotels in Chicago’s Loop

the Loop

This business district does not have much in the way of nightlife outside of the hotel lounges, and the restaurants are not that great for the money you dish out, but it is close to the city’s favored museums, Millennium Park, and the Lake Michigan shorefront.

Best Moderately-Priced Hotels in Chicago’s Loop

  • The Blackstone: While The Blackstone is part of a chain—the Renaissance Hotel—this masterpiece of luxury that is designated as a Chicago Landmark has a history of celebrity residents that include Hollywood starlets and leading men, as well as numerous presidents. The likes of FDR and John F. Kennedy stayed in one of the two penthouse suites, which consist of two rooms and two baths, high ceilings, portal-style windows that provide a perfect view of Lake Michigan, and giant skylights over the bed. For us normal folks, we get a moderately-priced room, which is $180-$270 a night in Chicago. While it is no penthouse, like most hotels in the city, you will get plenty of real estate. In other words, the rooms are quite large with marble entryways and mostly earth tones. Since its opening in 1910, it has undergone a few restorations and is now as hip as it is historic.
  • Hotel Monaco: The Hotel Monaco used to be a hat factory, but the prime spot that overlooks the Chicago River is better suited for incoming travelers, who will certainly appreciate the view. This hotel is in a great location, central to just about any attraction you will want to visit in the Loop, River North, and the Magnificent Mile. The Hotel Monaco brings you back in time with doormen and a huge lobby that has a fireplace and inviting chairs. The rooms have cushioned window seats with a view that inspires a sitting, large, decorative headboards above each bed, and a uniqueness that makes you feel at home.

Great Hotels on Chicago’s Magnificent Mile

Magnificent Mile
Magnificent Mile by Tony the Tiger on CC3.0

Serious shoppers will want to stay on The Magnificent Mile, in one of the many luxurious and offbeat boutique hotels on this strip. This area has a brisk pace, as it is the center of much of the action and is near the also-busy Oak Street Beach.

Best Moderately-Priced Hotel on Chicago’s Magnificent Mile

  • Drake Hotel: The Drake was once a big deal in Chicago. It was “the spot” for weary and rich travelers who required elegance and formality. It still has a Great Gatsby feel with a huge lobby, a harper plucking strings, and a tearoom. It isn’t really our style, but this place is an OG, a true Chicago legend built in 1920 in an Italian Renaissance style, so we had to visit it, especially considering that the prices are now manageable for normal folks like us. We were surprised to get a room for $140, but it was in late January and our view was limited. You pay a premium for windows facing Lake Michigan, regardless of the time of year.

Best Inexpensive Hotel on Chicago’s Magnificent Mile

  • Whitehall Hotel: Rumor is that the restaurant and lounge in the Whitehall Hotel were the first to serve alcohol after prohibition was abolished in 1932. I contend that they never stopped serving alcohol – under the table – and I dig that kind of joint. This sophisticated hotel is stylish and “cozy,” which isn’t necessarily a good thing for those looking for a big room, but at $100 for a spot on Chicago’s Magnificent Mile, accept the “coziness,” along with the friendly service and the great real estate.

Great Hotels in Chicago’s River North

River North Chicago

Night owls will love River North. West of the Magnificent Mile and north of downtown, young folks in their 20s and 30s make the rounds in their squads looking for a good time. An abundance of clubs and late-night restaurants dot this neighborhood, among a high density of hotels. Once an industrial area, the transformed neighborhood is THE nightlife district with fashionably dressed people flashing their wares.

Best Luxury Hotel in Chicago’s River North

  • The Langham: In Chicago, there are many places that resemble the staff and quarters found in the show Downton Abbey, but none more so than The Langham—might be because the hotel is London based. There are butlers on the premises and the service is stiff to the point of unnerving, but it is what makes this the very best 5-star hotel in Chicago. The rooms at The Langham are huge at 500-2,700 square feet, which is bigger than my house, so sneak in your friends and make a night of it—we did! The building was designed by pioneering architect Ludwig Mies van der Rohe, and you will see the depths of his creation once inside the steel and glass skyscraper. The artistry continues on The Langham’s walls with fine art galore, and the Travelle Bar and Lounge is about as romantic as it gets. Even though it is just on the second floor, it still has a magical view of the city.

Best Inexpensive Hotel in Chicago’s River North

  • Acme Hotel Company: The locally-owned hotel is quirky and delivers a great vibe for the cool couple without kids or the traveling single hipster. The rooms are pretty standard with dark hardwood floors, and cloth headboards with big handprints, which provides the art. There is a chalkboard on each hall door, which offers a place for guests to put messages, from “Do Not Disturb,” love notes, quotes, poetry, or whatever else might inspire you. Also, the Berkshire Room inside the Acme is a wonderful hotel bar that feels like a neighborhood spot.

Great Hotels on Chicago’s Gold Coast

Gold Coast Chicago

The rich folks that inhabit the “Gold Coast” gave the neighborhood its name. Nestled among 19th and 20th Century mansions, this ritzy residential area north of Downtown Chicago is a peaceful place to bring your big family, but you will pay for it. Within walking distance, you will find Michigan Avenue, the shore of Lake Michigan, Lincoln Park, and Old Town.

Best Luxury Hotel on Chicago’s Gold Coast

  • Waldorf Astoria: The Waldorf Astoria is lavish, so the Gold Coast is the perfect spot for it. While this hotel is branded as a chain, it is unlike the others. Initially, the hotel was the Elysian, built less than a decade ago, and taken over by Waldorf Astoria in 2012. The palatial palace of a hotel built like a French manor has a startlingly white lobby and rooms that are among the biggest in Chicago, with fireplaces and balconies with broad views of Chicago.

Best Moderately-Priced Hotel in Chicago’s Gold Coast

  • The Thompson: The Thompson is the spot where the locals go for a staycation. It is the hip place to go for an experience, unlike the many cookie-cutter hotels in town. The colors are vibrant, the room desks are made of glass, and sectionals occupy the space. The bathroom sinks are raised and the showers rain down on you. Along with friendly service and interesting art across the hotel, The Thompson’s Italian restaurant Nico Osteria is worth your time, with seafood-inspired plates.

Great Hotels in Chicago’s Lincoln Park

Lincoln Park Chicago
Nature Board Walk Lincoln Park by Alan Scott Walker on CC3.0

The price of accommodations goes way down in Lincoln Park. This neighborhood north of Downtown Chicago is a stylish plot that carries west toward Lake Michigan and houses the Lincoln Park Zoo. Here, you feel like a local, and is the perfect spot for big families and trendy folks alike.

Best Inexpensive Hotel in Chicago’s Lincoln Park

  • Hotel Lincoln: Hotel Lincoln is in a great spot for families. Outside of the Loop’s hustle and bustle, the hotel is across from Lake Michigan and the lauded Lincoln Park Zoo. When we arrived at the Lincoln Hotel, we were greeted by an energetic crew in bow ties and polka dots, who complimented us on our “smiles” and home state, which I assumed was a part of their strategy to keep those smiles on our faces. The quirky hotel has local art and vintage furnishings unique to each room. The lounge on the rooftop provides wonderful views of Chicago, and if you pay a little extra, you will get a view of the lake from your room. There is no need for a car; the hotel provides bikes and a pedicab to get you around the neighborhood.

Best Hostel in Chicago

Chicago Getaway Hostel
  • Chicago Getaway Hostel (Lincoln Park): If you want to see Chicago, and your budget isn’t where it needs to be to do it in style, you can rest your head for $40 a night at the Chicago Getaway Hostel. As a grown man, I did it once on a whim, and it served its purpose, though my top bunk was surrounded by several other bunks in a room filled with Russians. However, the staff was friendly, the kitchen was huge with modern appliances to prepare food, and there was a place to do laundry. The Chicago Getaway Hostel was super quiet compared to other hostels I have visited in the past. For people, who like to socialize at hostels, the quiet atmosphere might not work for you, and the common area is limited in its offerings, with a few tables and a small pool table. The Chicago Getaway Hostel is located in Lincoln Park and is a 15-minute walk to the L train, so while it is far away from the main action, you can get to it quickly by way of public transportation. The place is clean, and it is the cheapest place to stay in Chicago.

The Final Word on Chicago Accommodations

There is a systematic flow to Chicago, as the suits roll in through the week to conduct business or go to a seminar, and the weekends bring about touring families and weekending hipsters.

If you are surprised by a hotel rate quote, it is because you are visiting during a major conference, convention, or festival. Typically, Memorial Day through Labor Day brings the highest rates, while in the deepest and darkest depths of winter, you can find rates at 50 percent off the summer costs. However, expect to pay a lot any time of the year, and attempt to save money in other ways by taking public transportation, which is inexpensive and reliable, and staying away from the mini-bar and room service. You can find better places to eat in Chicago outside of your hotel, and at more reasonable prices, so get out of your room and explore one of America’s greatest cities.

Have Your Say?

Where is Your favorite place to Stay in Chicago? Do you have a favorite Hotel or a FAvourite District? Or have you stayed somewhere to avoid?! Let us know in the comments below or if you have any questions just fire away in the comments below.

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