Chicago is a huge city, stretching about 25 miles north to south along Lake Michigan and 15 miles east to west. The Loop, in the center, is the hub for business, theater, and tourism.
From there, the CTA transit system shoots out to the rest of the city, to neighborhoods like Hyde Park in the south, home to the University of Chicago and some of the city’s prettiest architecture, as well as the Museum of Science and Industry, or north up to Lakeview and Andersonville, quiet neighborhoods known for independent shops and restaurants. There’s the Gold Coast, a ritzy neighborhood close to downtown, and next to that is Lincoln Park, with high-end boutiques, cute restaurants, and a gorgeous, sprawling park and free zoo. To the west, you have West Loop, once an industrial district now known for buzzy restaurants and bars, and Wicker Park, full of vintage shops, great coffee, and packed with Chicago history.
Chicago is a city of neighborhoods––77 of them—each with their own vibe. It’s impossible to explore them all on one or even several trips, but getting out of downtown for at least a day is encouraged. Still, most hotels are concentrated in The Loop and the surrounding area. Expect to walk a lot on a trip to Chicago and make use of the CTA to get around.
Where to stay for the first time in Chicago: River North
The Loop is the heart of the city’s business and theater district and is conveniently located near most major attractions. River North is just over the Chicago River and has dozens of high-end restaurants, happy hour bars, and nightlife options. Both are easily accessible via the CTA and are well served by Uber, Lyft, and taxis. If this is your first time in the city, base yourself in one of these centrally-located neighborhoods.
Highlights:
- Walking distance to Millennium Park, where you can take photos of your reflection in Cloud Gate, aka “The Bean,” go ice skating in the winter or see free concerts and movies in the summer; the Art Institute is also right there.
- Steps from the Riverwalk, a 1.25-mile long path with art installations and restaurants
- Walking distance to all major Chicago theaters
- Easy access to multiple train and bus lines
- Food options for all price ranges, featuring cuisine from around the world
Freehand Chicago
This hostel is in a historic building and has one of the coolest cocktail bars in the city. The former Tokyo Hotel, built in 1927, was updated with funky decor and turned into a hostel in 2015. While most rooms are shared, there are private options for those who want their own space.
- Price: From $29 for a shared dorm to $171 for a private King room
- Vibe: Fun, eclectic hostel
- Wifi: Free
- Kid Friendly: While children are welcome, this hotel attracts a young adult crowd, and the bar and lobby area can be loud at night.
- Amenities: 24-hour front desk and security, fitness center, room service, parking, linens, and daily laundry, access to the cafe and Broken Shaker bar, special events, discounts on some city tours
- Website
Where to stay for nightlife in Chicago: River North
The Wit
ROOF, this hotel's rooftop bar, has an indoor/outdoor rooftop to keep the party going year-round. Here, you’ll find well-dressed Chicagoans and visitors dancing to a rotating lineup of DJs. Reservations are encouraged and easier to get for hotel guests. Outside of the bar, this is a four-star, modern hotel in a convenient location. Many rooms have views over the lake or downtown and spa-inspired bathrooms. There’s a restaurant on-site, as well as room service and a spa and fitness center.
- Price: Rooms from around $200
- Vibe: swanky, clean, convenient
- Wifi: Free
- Kid Friendly: This is a large Hilton hotel and attracts tourists of all kinds, but the nightclub and restaurants are not kid-friendly.
- Website
The Godfrey
The rooftop lounge at The Godfrey is a sunny lounge by day, bumping club by night. It has skyline views in all directions and igloos to keep you drinking outdoors even in frigid Chicago winters. Rooms are basic but spacious and modern.
- Price: Rooms from around $150
- Vibe: modern, boutique, young
- Wifi: Free
- Kid Friendly: No. The location is not ideal for families, as it’s not near most attractions for kids, and the crowd skews young adults or older businessmen.
- Website
Chicago Athletic Association
This former athletic club from the late 1800s was revamped in 2016, but designers kept the grand marble staircases and colorful art deco decor. The bathrooms and bedrooms, though, were updated to be modern and luxurious. Stay here for the walkable location and dining options. Cindy’s Rooftop Bar has sweeping views across Lake Michigan and Millennium Park, Milk Bar is one of the city’s most renowned cocktail bars, and you can play bocce or billiards in the game room or TopGolf in the Swing Suite. Oh, and there’s a Shake Shack.
- Price: Rooms from around $200 in the winter to $400 in the summer
- Vibe: Modern luxury with historic elements
- Wifi: Free
- Kid Friendly: With lots of space, on-site restaurant options like Shake Shack, and across the street from Millennium Park, this is a great family option.
- Amenities: Seven on-site restaurants, in-room dining, 24-hour fitness facility with personal training and group fitness classes, complimentary Heritage bicycles (weather permitting), concierge service, valet parking, pet-friendly
- Website
Where to stay with kids in Chicago: Navy Pier
On the east side of the city, jutting out into Lake Michigan, Navy Pier is packed with kid-friendly activities, like the Chicago Children’s Museum, the iconic Centennial Wheel and other rides, arcade games, fireworks every Wednesday in the summer, and more. There are also kid-friendly restaurants, including Chicago-style hot dogs, Chicago-style pizza, and Garrett’s popcorn. You can even take a Lake Michigan and Chicago River cruise steps from your hotel. Plus, it’s close to Museum Campus and directly on the Lakeshore Path. You can walk or bike over to the Field Museum, Shedd Aquarium, and Adler Planetarium on Museum Campus or take a water taxi in the summer.
Highlights:
- Packed with kid-friendly attractions and restaurants
- Water taxi to Museum Campus in the summer
- On the Lakeshore Path
Sable at Navy Pier, Curio Collection by Hilton
The Sable sits right on Navy Pier and has hundreds of windows that maximize the lake and skyline views. Combined with the blue and white color scheme and nautical decor, it almost feels like you’re on a giant ship.
- Price: From $250
- Vibe: Nautical, updated chain
- Wifi: Free
- Kid Friendly: This hotel is as close as you can get to the many family-friendly attractions on Navy Pier, and the staff is used to kids in the on-site restaurants and to accommodating extra beds, high chairs, and other necessary amenities.
- Amenities: The largest rooftop bar in the city, 24-hour fitness facility, views of the Wednesday night fireworks from most rooms, on-site dining, electric vehicle charging, streaming TV, wet bar, and mini fridge
- Website
Where to stay near attractions in Chicago: The Loop
The Loop is the heart of the city’s business and theater district and is conveniently located near most major attractions. It’s also where most metro lines meet, making it convenient for taking public transit elsewhere. From this neighborhood you can walk to Millennium Park, the Art Institute of Chicago, the Riverwalk and along the Lakefront Path. During the week, the Loop bustles with office workers (though less so in the years since the Covid-19 pandemic). It’s quieter on weekends, but if you’re in town to see a play or want to be somewhere easily accessible, this is the place to stay.
Highlights:
- Easily accessible via public transit; easy to access most other neighborhoods via the metro from the Loop
- Walking distance to the Riverwalk, Millennium Park and other attractions
- Close to the city’s major theaters, home to Broadway shows, the opera, ballet and more
- Plenty of dining options nearby
Hyatt Centric The Loop
Like most big brand hotels in The Loop, this one is fairly generic, but sometimes you need a reliable room in a good location for a mid-range price. The Hyatt Centric, like many buildings in the area, is housed in a historic Art Deco building and has a rooftop bar with craft cocktails and small plates. Rooms are spacious and comfortable, if not particularly unique.
- Price: Rooms from around $150
- Vibe: Classic, clean, convenient
- Wifi: Free
- Kid Friendly: This is a standard Hyatt hotel that has all the amenities you might expect from a large chain. Each floor has a section of rooms that can be booked together with an adjoining door.
- Amenities: Fitness center, meeting spaces, communal area with games and a fireplace, very centrally located, rooftop terrace, bathtubs
- Website
Palmer House Hilton
This historic hotel is famous for its gorgeous Beaux Arts lobby and a 19-century mural on the ceiling, but rooms have been updated with modern amenities. It’s right in the heart of the Loop, steps from the Chicago Theater, CIBC theater, and Nederlander theater, and minutes from Michigan Ave. and the Riverwalk. From the hotel, you can get virtually anywhere in the city using the L, which has stops about half a block away from the hotel in three directions. Fun fact: th
- Price: Rooms from around $250
- Vibe: Historic, elegant, convenient
- Wifi: Free
- Kid Friendly: Yes. This is a Hilton hotel, so has all the standard amenities you would expect from a large chain hotel, including cot rental.
- Amenities: Spa, Fitness center, meeting spaces, beautiful lobby bar with live music on weekends, restaurant on-site, room service, magic shows.
- Website
Where to stay with family in Chicago: Lincoln Park
Lincoln Park, north of downtown and on the east side of the city, near the lake, is a great option for families because it’s close to major attractions but has much more of a neighborhood vibe. There are great boutiques and dining options and beautiful homes to ogle while walking around the neighborhood. You’re also near the actual Lincoln Park, a 1,200-acre park with a free zoo, botanic garden, and historic statues. Lincoln Park is well-connected with the Red and Brown CTA lines, as well as many bus lines. In addition to hotels, Lincoln Park has lots of cute home rentals.
Highlights:
- Next to Lincoln Park Zoo, the botanic gardens, a nature museum, and walking trails
- Steps from restaurants and boutiques
- Quiet yet convenient
- Easy access to tourist attractions via the CTA. About 20 minutes via the CTA to the Loop, and 35 minutes to Museum Campus.
Hotel Lincoln
This hotel dates back to the 1920s and is filled with vintage details and pieces from local artists. It’s directly across from the park and the massive Green City Market (Saturday mornings from April–November) and within walking distance to The Second City and plenty of restaurants and shops. The rooftop bar is enclosed, so you can even admire the skyline in snowy weather.
- Price: From $150
- Vibe: Quirky, historic
- Wifi: Free
- Kid Friendly: This hotel is across the street from the zoo, park and beach and has extra beds and cribs available. Pets stay for free, too.
- Amenities: Enclosed rooftop bar, on-site restaurant, on-site coffee shop, bike rentals, rooftop yoga, 24-hour fitness center
- Website
Lincoln Park Guest House
This boutique guest house is perfect for parents visiting students at DePaul University (it’s across the street) or for those who want to feel more like they live in the neighborhood. It’s a five-minute walk to the train and steps from a Divvy bike station. The king beds are extremely comfortable, and the rooms are dark and quiet, despite being so close to the center of the city.
- Price: From $339
- Vibe: Boutique, bed & breakfast
- Wifi: Free
- Kid Friendly: No. Each room sleeps two, and unlike a hotel, additional beds are not available.
- Amenities: Free parking, coffee, and tea, writing desk, book selection, mini fridge
- Website
Where to stay for one night in Chicago: Wicker Park
Wicker Park, on Chicago’s westside, is one of the city’s coolest neighborhoods for its coffee shops, boutiques, record stores, award-winning bars and restaurants, and overall vibe. But if you only have one night in the city, you should stay here because it’s on the CTA Blue Line, meaning you can get to and from the airport in about 30 minutes. It is by far the most convenient neighborhood that still also has things to do.
Highlights
- On the Blue Line
- Tons of dining options, bookstores, and other shops
- Fun, neighborhood feel
The Robey
One of Chicago’s most iconic buildings, the 1929 art deco Northwest Tower was one of the first skyscrapers built outside of downtown. It was turned into a boutique hotel in 2016 but still pays homage to its past with dark-paneled walls, leather furniture, and emerald accents. Thanks to its triangular shape, every room gets a lot of light. Most importantly, it has a great restaurant and bar and is steps from the Blue Line, ideal for a one-night stay.
- Price: From $200
- Vibe: Historic, hip
- Wifi: Free
- Kid Friendly: The crowd at this hotel skews toward couples and groups of friends, but kids are welcome, and it does have extra cribs and beds on-site. There’s a Walgreens next door, which past visitors have pointed out is convenient for parents who might need diapers, medicine, or other last-minute items.
- Amenities: Amenities from Le Labo, soft denim robes, on-site cafe, rooftop cocktail bar and pool, bikes available, valet parking
- Website
Where to stay for a romantic trip to Chicago: Gold Coast
A walk through this historic district of Chicago screams glamor and old money. The mansions are beautiful but not ostentatious, the gardens are gorgeous, the lake views swoon-worthy, the hidden restaurants and their twinkling lights and gardens are made for romantic date nights, and the location is perfect for long walks through Lincoln Park, a sprawling park north of downtown or along the Lakeshore Path, where you can see Lake Michigan to the east and skyline views to the south.
Highlights:
- Steps from the lake and Lincoln Park; easy access to downtown and other neighborhoods
- One of the prettiest parts of Chicago
- Plenty of romantic restaurants and bars nearby
The Drake
Like so many historic Chicago hotels, this one opened in the early 1900s and has been a favorite of politicians and celebrities ever since. Barack Obama and Princess Diana have both stayed here. The Italian Renaissance Revival style gives it a romantic feel, with its arched walkways, sweeping staircases, and ornate ceilings. The rooms are luxurious. Think plush beds, marble baths, and high-end bath products.
- Price: From $150
- Vibe: Old-school luxury
- Wifi: Free
- Kid Friendly: Yes. The hotel partners with a babysitting service and has spacious rooms with pullout sofa beds, kids menus, and can also provide beds for your children’s dolls.
- Amenities: High-end bath products, mini-bar, coffee maker, on-site convenience store, on-site coffee shop, on-site souvenir store
- Website
Viceroy Chicago
This stylish hotel is in a landmark building and has rooms with views of Lake Michigan and a great rooftop bar and pool. Rooms are decorated in black and gold, with mid-century modern furniture.
- Price: From $250
- Vibe: Modern luxury
- Wifi: Free
- Kid Friendly: Rooms are on the larger side, and the hotel is near a number of attractions, but the crowd does not include a lot of families.
- Amenities: On-site restaurant and rooftop bar and pool, rain showers, large work desks, fitness center, luxury bath products
- Website
Where to stay on a budget in Chicago: Lakeview
Lakeview is, exactly like it sounds, on the lake, which makes it sound expensive. But this northside gem is one of the most affordable neighborhoods in the city. Walk down North Broadway or Halsted, both packed with affordable bars, restaurants, thrift stores, wine shops, and more, or head to Wrigley Field to catch a Cubs game. This is also home to the first recognized gay neighborhood in the US, once dubbed Boystown and now called Northalsted, and retains a welcoming vibe and plenty of LGBTQ+-friendly bars.
Highlights:
- Feels like living in a neighborhood, but easy to get downtown on the Red Line or several buses
- Affordable while still having a lot to do
- Very fun, very chill
- Close to the lake
Best Western Plus Hawthorne Terrace
This small branch of the Best Western chain is one of the few hotels in the area and has large rooms that are steps away from the Lake and the many restaurants and bars of the Northalsted neighborhood. Some rooms include in-suite kitchens, which are nice for making your own food and saving money on longer stays. There’s free coffee all day, and the pretty courtyard outside makes a great place to sip it while people-watching.
- Price: From $120
- Vibe: Cute, budget
- Wifi: Free
- Kid Friendly: The hotel offers all amenities you would expect from a large chain and is close to Wrigley Field.
- Amenities: Fitness center, pet-friendly, parking, complimentary breakfast
- Website
Wrigley Hostel
The Wrigley Hostel location is pretty hard to beat if you’re a baseball fan, and it’s by far the most affordable game-day option. You’ll be a two-minute walk to Wrigley Field but also close to the Red Line, which gets you downtown in minutes. In the neighborhood, you’ll find dozens of bars, Chicago-style pizza, and plenty of other restaurants, cafes, comedy clubs, shopping, and more.
- Price: Dorms from $38, private rooms from $180
- Vibe: Convenient, affordable, clean
- Wifi: Free
- Kid Friendly: Rooms are shared, and most clientele is under the age of 30.
- Amenities: Full kitchen; outdoor lounge with a grill; common room with a pool table, shuffleboard and TV; computer room; free library; free lockers; coffee and tea all day; weekly bar crawls, pizza nights and other events
- Website
