Where to Stay in Chicago

By Santorini Dave

My Favorite Hotels in Chicago

• Best location: Langham Hotel
• 5-star hotel: Peninsula
• 4-star hotel: Blackstone
• 3-star hotel: Omni
• Hotel for couples: Ivy Boutique
• Hotel for families: Four Seasons

The Chicago River divides the Loop from the River North neighborhood. Many hotels are located just north or south of the river and are excellent for first-time visitors. Just north of the river: Langham • Sheraton Grand Riverwalk • Loews • InterContinental Magnificent Mile. Just south of the river: Royal Sonesta • LondonHouse • Hyatt Regency • Swissôtel.

The Best Areas to Stay in Chicago

• Chicago Hotel Map

One of my favorite American cities, Chicago is known for jazz music, Prohibition-era gangsters, their signature deep-dish pizza, and pioneering architecture – seriously, if you do nothing else here, take the Chicago River Architecture Cruise. The city is crammed with fabulous places to stay, from luxurious five-star hotels to hip hostels, and many good-value options in-between. Most hotels lie in the city center, but more choices are springing up in Chicago’s dynamic outer neighborhoods.

My wife and I enjoying some deep dish pizza in Chicago.

Most of the Windy City’s biggest attractions are in or close to The Loop, the downtown area roughly bounded by the central “loop” of the “L” Train and the shore of Lake Michigan. Today, much of Downtown’s commercial activity – and some of the best restaurants and bars in the city – have spread beyond the Loop to adjacent districts: South Loop, West Loop, and the famous shopping strip of Magnificent Mile, which separates the River North and Streeterville districts. This barely scratches the surface, however – Chicago sprawls for well over 25 miles in all directions from here, a patchwork of neighborhoods and suburban communities dubbed “Chicagoland”. (Be aware that the total tax added to hotel rooms in Chicago adds up to 17.4 percent, apartments and home share rentals are taxed 23.4 percent).

While it’s relatively easy to explore the city center on foot, Chicago’s outer neighborhoods cover a vast area that is best approached by Chicago Transit Authority’s 24-hour L Train network, Metra trains, or taxis and Uber/Lyft. If driving yourself, be prepared for overnight parking rates of up to $50 at top hotels in the city center.

Best Places to Stay in Chicago

The Langham Hotel, one of the city’s best luxury hotels, is located in River North and directly on the Chicago River.

• Best Luxury Hotels in Chicago
  Langham • Peninsula • Four Seasons • Palmer House Hilton • Waldorf Astoria
• Best Chicago Hotels for Families
  Four Seasons • Hilton • InterContinental Magnificent Mile • Swissôtel
• Best Boutique Hotels for Couples
  Silversmith • Ivy Boutique Hotel • Staypineapple • Sono
• Best Midrange/4-Star Hotels in Chicago
  Fairmont Millennium Park • Chicago Athletic Association • Blackstone • InterContinental Magnificent Mile • Omni Chicago All Suites Hotel-Magnificent Mile
• Best Budget Hotels in Chicago
  HI Chicago Hostel • Freehand

Our suite at Fairmont Millennium Park.

A Premium King room at the Silversmith, the best boutique hotel in Chicago, located in the Loop.

Best Areas in Chicago for…

• Best Neighborhood for First Time Visitors: The Loop (Downtown Chicago)
  The Loop is the Chicago of popular imagination. All the big attractions are here or within strolling distance, and the whole district is an architectural showcase with some of the earliest skyscrapers in America standing side-by-side with modern glass and steel giants such as the Willis Tower (the third-largest building in the US). Adjacent Millennium Park and Grant Park make for pleasant green waterfront escapes, along Lake Michigan, while Chicago River boat trips take in the best city views. The Loop is at the hub of the city’s public transport network, making it easy to reach anywhere else in the city. The Palmer House Hilton (luxury) and the Hampton Inn Theatre District (midrange) are great places to stay for first timers to Chicago.
• Best Neighborhoods for Families: South Loop and Lake Shore East
  Both the South Loop and Lake Shore East (AKA New Eastside) are popular with families for accessibility to Chicago’s best kid-friendly attractions, plus great hotels, and a calmer vibe than the main downtown core of the Loop. South Loop is near the Field Museum of Natural History, Shedd Aquarium, and the Adler Planetarium, while Lake Shore East sits on the Chicago Riverwalk, a riverside pedestrian pathway lined with restaurants, museums, and public art plus boat tours and kayak rentals.


Skyscrapers in the Lake Shore East neighborhood overlook the Bean and Jay Pritzker Pavilion in Millennium Park and the adjacent Loop neighborhood. DuSable Harbor and Lake Michigan are in the background.

• Most Romantic Neighborhoods: Oak Park and Gold Coast
  The birthplace of Ernest Hemingway and the home of Frank Lloyd Wright, the village of Oak Park just outside of the city offers all the charm of Chicago in a smaller, cuter package. Known as an artists’ enclave, this small town offers top-notch theater, live music, dining, vintage architecture, historic sights, and nightlife in a compact space brimming with romantic inns and B&Bs. For a location closer to downtown Chicago, couples should consider Gold Coast, Chicago’s luxury neighborhood on Lake Michigan. Here picturesque streets, posh boutiques, and high-end restaurants abound, along with some chic hotels. Other than Oak Street Beach and luxury shopping, there’s not much in the way of specific attractions here, though restaurants such as steakhouse Maple & Ash and stylish 3 Arts Club Café have become destinations in their own right.
• Best Neighborhood for Nightlife: River North
  River North (as the name suggests, the neighborhood just north of the Chicago River and the Loop), is one of Chicago’s liveliest neighborhoods, especially at night. Staying here means easy access to a plethora of top eateries and some of the best bars and clubs in the city. Enjoy the classic tiki bar vibe at Three Dots and a Dash, live music at plush cocktail lounge Bassment, or drinks at TAO Chicago, an Asian-themed restaurant that morphs into a fashionable nightclub. Cheaper drinks are available at no-frills neighborhood bottle-shop-cum-bar Rossi’s, while proper Guinness is served at The Kerryman. Visitors will also find House of Blues Chicago here. From River North its just a short train ride or half-hour walk to Old Town, another nightlife hub, home to legendary comedy club The Second City.


The Architecture Cruise is a must for first time visitors.

• Best Neighborhood for Food and Restaurants: West Loop
  This former industrial and meatpacking district – just to the west of the Loop, across the Chicago River – is now home to the most dynamic food scene in the city. Some of the biggest names in culinary America are here: the best burgers anywhere at Au Cheval, Stephanie Izard’s Girl and the Goat, old-school Italian sandwiches at J.P. Graziano Grocery, classic diner Lou Mitchell’s, and world-famous cocktail lounge The Aviary. The West Loop is also home to Greektown, crammed with authentic bakeries and restaurants, especially along South Halstead Street. Though there’s not much in the way of attractions beyond restaurants, staying in West Loop means being within walking distance or a short cab ride of all the sights in the Loop itself.
• Best Neighborhoods for Shopping: River North, Streeterville, and Gold Coast
  Home of the Magnificent Mile, the Streeterville and River North districts are the obvious choices for serious shoppers. Mag Mile (officially Michigan Avenue) has been one of the most famous shopping areas in the world for years, and remains crammed with a vast array of stores, from Levi’s and Burberry to Louis Vuitton and Neiman Marcus. The street itself terminates at the southern end of Gold Coast, where shoppers will delight in the array of luxury boutiques and designer stores in Chicago’s most affluent neighborhood. En route, there are plenty of sights in between the shops, notably the John Hancock Building and the Historic Water Tower.


Our view of a Cubs game from a rooftop apartment near Wrigley Field.

• Best Neighborhoods for a Local Vibe: Wicker Park and Bucktown
  Beyond Downtown, Chicago is a vast patchwork of neighborhoods full of local color. Wicker Park and Bucktown are both excellent choices for living like a local. These off-the-beaten-track districts are crammed with vintage stores, hip cafés, a diverse array of restaurants and bars, bookstores, art galleries, and unique shops that seem light-years away from the tourist hotspots of central Chicago.
• Unsafe Areas of Chicago
  Central Chicago is generally quite safe, though the usual precautions should be taken at night. South Side Chicago (with the notable exception of the Hyde Park area) still suffers from high levels of crime and one of the highest murder rates in the US, but there’s no reason for most travelers to venture here.

The Best Places in Chicago for Tourists

1. The Loop (Downtown Chicago)

The Loop encompasses most of Downtown Chicago, a forest of giant skyscrapers packed in between the Chicago River and Lake Michigan. Willis Tower is here (with its 103rd-floor Skydeck Chicago at 1353ft up, as well as the Theatre District and iconic Chicago Board of Trade. Other major attractions include the world-class Art Institute of Chicago, the American Writers Museum, and the future location of the Chicago Blues Experience. The greenbelt on the lakefront includes Grant Park and Millennium Park with its giant stainless-steel “Cloud Gate” sculpture, better known as “The Bean”. The Jay Pritzker Pavilion in the park hosts the annual Chicago Blues Festival and Chicago Jazz Festival.

• Best Hotels: Palmer House Hilton • Chicago Athletic Association • Blackstone • Silversmith • Hilton • Staypineapple • Hampton Inn Theatre District

2. The Magnificent Mile/River North/Streeterville

Running north along Michigan Avenue from the Loop, just across the Chicago River, the Magnificent Mile (“Mag Mile”), is still Chicago’s prime shopping district. Today the strip’s iconic 1920s skyscrapers such as the Wrigley Building and the Tribune Tower are interspersed with modern shopping malls and newer towers such as the John Hancock Building (with its 360 Chicago observation deck). Also here is the Chicago Sports Museum. River North lies on the west side of Mag Mile, now a stylish neighborhood of art galleries, restaurants, and nightclubs set in former warehouses. River North also features theMART, a converted office building full of design showrooms, Eataly Chicago, Holy Name Cathedral, and antique-packed Driehaus Museum. The district on the east side of Mag Mile, lining the Lake Michigan waterfront north of the Loop, is Streeterville, a buzzing enclave comprising high-rise condos, offices, and stores. It’s also home to the cutting-edge Museum of Contemporary Art as well as family-friendly Navy Pier – a popular landmark crammed with attractions: the 200-foot Centennial Wheel, Chicago Children’s Museum, IMAX Theater, Chicago Shakespeare Theater, and several restaurants and cafés. It’s also a great place to take a sightseeing cruise or just enjoy the views of Chicago’s downtown. There’s even a safe place to swim nearby at Ohio Street Beach.

• Best Hotels: Peninsula • Langham • InterContinental Magnificent Mile • Omni Chicago All Suites Hotel-Magnificent Mile • Loews • Ivy Boutique Hotel

3. Gold Coast

Founded by a handful of millionaires after the Great Chicago Fire in the late 19th-century, Gold Coast has been the most well-to-do neighborhood of Chicago since its inception. Residential streets here are lined with historic mansions and luxury high-rises. Oak Street is particularly popular for high-end shopping at designer stores and specialty boutiques, while Rush Street is home to some of Chicago’s most exciting restaurants, craft cocktail lounges, and a handful of nightclubs with dancing until dawn. Sandy Oak Street Beach is a popular swimming spot with lifeguards on duty. Though there are not a ton of attractions here, aside from the curious International Museum of Surgical Science, its prime location adjacent to Streeterville, Lincoln Park, and Old Town make it an excellent home base for exploring the city.

• Best Hotels: Four Seasons • Waldorf Astoria • Ritz-Carlton • Park Hyatt • Sofitel Magnificent Mile

4. Lake Shore East

Also known as New Eastside, this master-planned neighborhood is actually part of the Loop, located at its northeastern corner. This area is home to the fantastic Chicago Architecture Center, known for its intricate, 40,000-building model city as well as its outstanding walking, boat, bus, and train tours of Chicago and the surrounding areas. Lake Shore East Park in the heart of the neighborhood is a tiny green oasis with botanical gardens and a playground. As a younger neighborhood, expect to see plenty of contemporary skyscrapers, most notably the Aqua with its distinctive wave-like façade. With a prime perch right on the Chicago Riverwalk and bordering Millennium Park, this family-friendly area allows easy access to the best-loved sights of the city paired with quieter, cleaner streets than you’ll find elsewhere inside the Loop.

• Best Hotels: Fairmont Millennium Park • Swissôtel

5. West Loop

Most of West Loop lies within walking distance of the attractions in the Loop itself (the city’s main stations, the Ogilvie Transportation Center, and Amtrak’s Union Station, are also here), but its main draw is food. Staying here means easy access to some of Chicago’s best restaurants, diners, noodle shops, taquerias, and cafés, many of them in the former warehouses of the hip Fulton Market district. Attractions in West Loop include Old St. Patrick’s Catholic Church, the monthly Randolph Street Market, and the National Hellenic Museum in Greektown, also home to Greek restaurants, bakeries and stores.

• Best Hotels: Emily Hotel • Hoxton • Hyatt House West Loop • Homewood Suites Downtown West Loop • Nobu

6. South Loop

South Loop is a primarily modern residential neighborhood south of Downtown. Popular with families, its main appeal is its proximity to the lakefront Museum Campus comprising the Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium. It’s also home to Soldier Field (the iconic Chicago Bears stadium), legendary Chess Records (run by Willie Dixon’s Blues Heaven Foundation, open for tours), and the charming Prairie Avenue District. Hotels in South Loop tend to be a little better value than in other Downtown neighborhoods, though prices rise during major events at the McCormick Place Convention Center. From the South Loop, it’s just a short drive or train ride to Pilsen, a lively Latin neighborhood home to famed live venue Thalia Hall, the Punch House bar, and live piano bar Tack Room.

• Best Hotels: Hampton Inn McCormick Place • Homewood Suites Downtown South Loop • Hyatt Regency McCormick Place • Marriott Marquis

7. Lincoln Park

Around two miles north of the Loop, Chicago’s largest green space lends its name to the surrounding neighborhood of leafy streets and stately townhouses. It’s a safe, generally laid-back district ideal for families. Lincoln Park itself – which contains the Peggy Notebaert Nature Museum, Conservatory, a zoo, and numerous monuments – is the main attraction here, though there’s plenty of high-end shopping, eating, and drinking along North Clark and North Halstead streets (including world-famous Alinea). The Chicago History Museum is also here, as well as a couple of family-oriented beaches on Lake Michigan.

• Best Hotels: Villa D’ Citta Bed & Breakfast • Willows • Lincoln • Versey Days Inn

8. Boystown/Lakeview

North of Lincoln Park, Northalsted is better known as Boystown, one of the most famous (and oldest) LGBTQ+ communities in the United States. It’s known for its buzzing nightlife, LGBTQ-owned businesses, excellent restaurants, plus Legacy Walk, the world’s first outdoor LGBTQ history museum. Boystown is located inside the larger neighborhood of Lakeview, which is also home to historic Wrigley Field, home of the Cubs and open year-round for tours.

• Best Hotels: Majestic • Best Western Plus Hawthorne Terrace

9. Hyde Park

Six miles south of the Loop, Hyde Park is the most upscale neighborhood on the South Side, famous for being home to the University of Chicago, the Obama family and several decent museums. It’s also slated to be the future location of the Obama Presidential Center. The vast Museum of Science and Industry is the major highlight here, along with the DuSable Museum of African American History. Hyde Park is just 15 minutes from the Loop via Metra Electric District trains, but its leafy streets and diverse population makes staying here a fascinating contrast from Downtown.

• Best Hotels: Sophy Hyde Park • Hyatt Place Chicago-South/University Medical Center

10. Oak Park

Though it officially lies beyond the city’s western boundary some nine miles west of the Loop (around 25 minutes on the Green Line ‘L” train), charming Oak Park has long been part of the greater Chicago urban sprawl. Its quiet, leafy streets feature small parks, cozy cafés, and a handful of fascinating sights: Ernest Hemingway’s Birthplace Museum, where the author spent his early childhood, and the Frank Lloyd Wright Home and Studio. Wright also designed the nearby Unity Temple, widely considered the “first modern building in the world”.

• Best Hotels: Carleton of Oak Park • Harvey House Bed & Breakfast

11. Wicker Park/Bucktown

Just over two miles northwest of the Loop, on the west side of the Chicago River are two vibrant communities, Wicker Park and Bucktown, for a more local-style experience of the city. The heart of Wicker Park is the “Six Corners” area where North, Milwaukee, and Damen Avenues intersect, a short walk from the Damen “L” station. North Milwaukee Avenue is the main drag of Wicker Park, known for its lively nightlife, while bustling North Damen Avenue runs through Bucktown. Check out nightlife hotspots Subterranean, Davenport’s Piano Bar, and cocktail pioneer The Violet Hour, or head up to the Cabana Club terrace bar at The Robey for views across the whole city. In Bucktown check out local favorites, the Map Room bar and the 1920s ice cream parlor Margie’s Candies. In addition to the Robey, top hotels in the area include Wicker Park Inn, cozy Ray’s Bucktown Bed and Breakfast. Both neighborhoods are easily accessible via the Blue Line “L” (7–10 minutes from the Clark/Lake station in the Loop) .

• Best Hotels: Robey • Wicker Park Inn • Ray’s Bucktown Bed and Breakfast

The Best Hotels in Chicago

1. The Peninsula Chicago – River North

Hotel phone: 312.337.2888
Gorgeous, contemporary luxury, with the most intuitive and gracious service in the city. Built in this millennium, but designed in Art Deco style with vertical accents, high ceilings, and golden domes. Each room is completely controlled via tablet, from temperature to lighting, and all suites include a complimentary three-hour chauffeured tour of the city in a Mini Cooper. Their full-service spa takes up two full stories, plus they have a heated pool and whirlpool. They are also home to the best Chinese restaurant in the city. Located on the Magnificent Mile in the Near North area, close to the Museum of Contemporary Art and the Water Tower.

2. The Langham Chicago – River North

Hotel phone: 312.923.9988
An elegant newly-awarded five star, five diamond property on State Street. The Langham is home to Chuan Spa, the only five star spa in Chicago, offering a full menu of treatments, plus a Himalayan salt sauna, lavender steam room, herbal warm room, eucalyptus steam shower, and an indoor pool. The Pavilion hosts the finest afternoon tea service in the city, with sweet and savory treats and live music. Located on the north side of the Chicago River, steps from shopping and dining, this is a superb choice for experience the best the city has to offer.

3. Four Seasons Chicago – Gold Coast

Hotel phone: 312.280.8800
Classic, luxury hotel at the start of the Magnificent Mile, with the highest luxury guest rooms in the city and unmatched city and lake views. An art-forward hotel, they have eleven museum-quality works here, which guests may tour through. This hotel has several suite options, many of which have kitchenettes. This is an excellent choice for families, offering tons of kid-friendly amenities; including a teen spa, kids’ club, and indoor pool. Connected to the 900 North Michigan Shops, walking distance to Oak Street Beach and the John Hancock building.

4. The Palmer House – The Loop

Hotel phone: 312.726.7500
A stately and historically significant luxury hotel in the heart of Chicago. The Palmer House is the city’s longest continually opened hotel, since 1871. Every U.S. president since Grant has either slept or dined here, Mark Twain spoke here, and the trial over General Custer’s death took place here. Interiors feature vaulted, hand-painted ceilings, gold detail, and marble columns. Indoor pool and full service spa on site. Well-situated in the Loop, near The Art Institute, Millennium Park, and the Chicago Symphony.

5. The Blackstone – The Loop

Hotel phone: 312.447.0955
Beaux-Arts luxury hotel that’s rich in history. This is home to the original “smoke-filled room” where a secret meeting selected Harding to run for president, as well as Al Capone’s barber shop. Breathtaking interiors have been lovingly restored to preserve its unique feel. Phenomenal Spanish tapas restaurant on site. Located in the Cultural Mile, south end of the Loop, The Blackstone is close to the Art Institute and Museum Campus.

6. Waldorf Astoria Chicago – Gold Coast

Hotel phone: 312.646.1300
Chic hotel with an urban luxury vibe, modeled after Parisian styles of the ‘20s. Their guest room options include suites with fireplaces and balconies. This hotel houses an award-winning spa, plus nail salon, hot tub, and a pool with family swim hours. Located in the luxe Gold Coast neighborhood, the Waldorf Astoria is situated in a little triangle between shopping on State Street and dining on Rush Street, walking distance to Oak Street Beach and the Mag Mile.

7. The Ritz-Carlton, Chicago – Gold Coast

Hotel phone: 312.266.1000
Gorgous hotel just off the Magnificent Mile with amazing city, lake, and Navy Pier views. This hotel offers gorgeous rooms and a wide range of suite options, some with two floors, two bedrooms, or full kitchens. Amazing food and drink options here include a fine dining brasserie and a rooftop bar serving late night tapas and cocktails. Be sure to start the morning with a rooftop yoga session or a dip in the pool. Walking distance to Water Tower Place, the Museum of Contemporary Art, and the Driehaus Museum.

8. Chicago Athletic Association Hotel – The Loop

Hotel phone: 312.940.3552
The most unique hotel in Chicago, originally built as a men’s sporting club in 1890 and completely renovated in 2015. This hotel offers luxury, sport-themed accommodations with cool details, like pommel horse benches and tennis racket nightstands in the rooms, all amid the original architectural beauty of mosaic tile floors, carved wood accents, and gold ceilings. Five excellent restaurants and bars onsite, with a game room and grand lobby library. Located in the Loop, near the Art Institute of Chicago and Millennium Park, overlooking The Bean.

9. Park Hyatt Chicago – Gold Coast

Hotel phone: 312.335.1234
Contemporary and stylish luxury hotel in the Gold Coast with views of the Water Tower and lake. This hotel offers spacious rooms, all with Eames chairs and window seats. Dining is fantastic here, with NoMi Kitchen and Lounge offering modern American fare and seasonal cocktails, plus an extensive wine variety and cheese cave. Their art collection boasts an original Matisse and Chihuly glass art, while their lobby displays a wild collection of fossils and meteorites. A spa, pool, and sun terrace round out the experience. Walking distance to upscale shopping and great restaurants.

10. InterContinental Chicago – Streeterville

Hotel phone: 312.944.4100
Luxe hotel right on the Chicago River and boasting a restored Art Deco pool with stained glass and columns. The décor here is a fusion of cultures and times, Assyrian to Celtic, Medieval to modern, but the hospitality is true Midwestern warmth. There’s a great little wine tasting room here, pairing drinks with chocolates and cheeses. Just a short walk to the Chicago Architecture Foundation River Cruise and The Bean.

11. Omni Chicago – Streeterville

Hotel phone: 312.944.6664
Sophisticated, all-suite, luxury hotel located on the Mag Mile. Lots of room options, including some with sleeper sofas, full kitchens, and extra half baths. Popular with foodies, The Omni’s signature 676 Restaurant & Bar cures their own charcuterie and makes their own drink infusions and mixes-in house. For a hands-on experience, check out one of their packages for a deep dish pizza-making or a wine and food pairing class. Other amenities include a pool, hot tub, spa, and sun deck. Near the Water Tower and the Museum of Contemporary Arts.

12. Sofitel Chicago – Gold Coast

Hotel phone: 312.324.4000
French-brand luxury hotel with international flare; over 20 languages are spoken here, even among the bartenders. The building itself is built on a slant, giving each room an unobstructed view of the city and Lake Michigan. Gorgeous modern interiors include their Parisian-inspired opera staircase, lit with subtle, glimmering lights at night. Upscale shopping and fine dining is right outside the door, while the Museum of Contemporary Art is only a short walk away.

13. Loews Chicago – Streeterville

Hotel phone: 312.840.6600
Lavish luxury hotel perfectly located just five minutes’ walk to the Mag Mile, Millennium Park, and Navy Pier. This hotel is ideal for family stays with several room and suite options, plus fun amenities, like “dive in movies” at their pool and a full lawn on an elevated terrace. With great Argentine restaurant and full service spa, this is also a great pick for a relaxing and indulgent stay.

14. Fairmont Millennium Park – Lake Shore East

Hotel phone: 312.565.8000
With its V-shape, the Fairmont Chicago offers stunning views of Lake Michigan, Navy Pier, or Millennium Park from nearly every room. This hotel connects to the Pedway, Chicago’s underground walking system, so guests can get around town even in the worst weather without a coat. Enjoy the soothing onsite spa and cap the night off with a cocktail in their gorgeous brass-circled lobby lounge. Fantastic shops, restaurants, and the architectural boat tour are right at your doorstep.

15. The Drake – Gold Coast

Hotel phone: 312.787.2200
Quintessential luxury in an Art Deco building on Oak Street Beach. This hotel has long played host to the well-heeled, including Princess Di (they even named a suite for her). There are five restaurants onsite, but they are best known for their afternoon tea service, featuring a live harpist. For children they offer a Little Prince or Little Princess tea service. Other family friendly bonuses include suites with two bathrooms, an American Girl package, and their proximity to Lego Land in Water Tower Place.

16. Swissotel Chicago – Lake Shore East

Hotel phone: 312.565.0565
This sleek hotel is shaped like a three-sided prism to offer panoramic river, lake, and city views, while its central location makes this hotel a great home base for exploring Chicago. For families, they offer connecting or adjacent kids’ rooms, stocked with age-appropriate amenities for ages 0-17. For couples or solo travelers, they have a lively lobby bar. An indoor pool, whirlpool, spa, and sauna fill out the range of amenities, making this a perfect stay for mixed groups. Located on the Chicago Riverwalk, near the Chicago Architecture Foundation River Cruise and The Bean.

17. Millennium Knickerbocker Hotel – Gold Coast

Hotel phone: 312.751.8100
Spectacular, Art Deco luxury hotel, formerly home to Al Capone’s secret casino, and later a Playboy hotel. Built at the height of the roaring ‘20s, this hotel features its restored, original light-up dance floor, plus grand, ornate gold and original plasterwork. Wonderful location, right next door to the John Hancock building and walking distance to most attractions, including the Bean, plus great restaurants on Rush Street

18. Kimpton Hotel Monaco – The Loop

Hotel phone: 312.960.8500
Boutique-style, luxury hotel in a hundred-year-old former hat factory. Most rooms have city or lake views and window seats, which they make up as beds for children. This hotel is fantastic for families, with tons of unique amenities, including loaner goldfish, hula hoops, and kid-sized bathrobes. Superb bar and restaurant onsite, serving Midwest comfort food, brewing their own beer, and mixing inspired craft cocktails. Fantastic location in the Loop, near the river, shopping, and nightlife.

19. Thompson Chicago – Gold Coast

Hotel phone: 312.266.2100
Modern luxury hotel one block off the Magnificent Mile. This hotel features provocative artwork and eclectic décor. The Thompson is well known for their outstanding level of service at every interaction. The fab kitchen here serves great rustic, Italian food as well as a stellar weekend brunch. Located in the Gold Coast, walking distance to Oak Street Beach, as well as the finest shopping in the city.

20. Allegro Royal Sonesta – The Loop

Hotel phone: 312.236.0123
Glamorous Art Deco hotel in the Theater District area of the Loop. Decadent retro interiors with original molding and lighting, plus vintage inspired décor. Suites are twice the size of rooms, and higher floors offer sweeping city views. Enjoy yoga gear in each room and a complimentary wine reception every evening. This hotel is surrounded by shopping and restaurants and is within walking distance to The Bean, Chicago Theater, and the river.

21. JW Marriott Chicago – The Loop

Hotel phone: 312.660.8200
Luxury hotel in a historic Daniel Burnham building with polished marble and rich gold details. Built in 1914 and recently restored, this Chicago landmark has an indoor pool, whirlpool, and sauna. Dine well at their gourmet Italian restaurant or in their New American-style lounge. Centrally located in the Loop, near Millennium Park and Navy Pier.

22. St. Jane – The Loop

Hotel phone: 312.345.1000
Grand hotel in a historic Art Deco building. The building itself, designed after a green champagne bottle with a golf foil top, perfectly suits the indulgent attitude the hotel represents. The interiors feature luxurious fabrics, elegant granite and marble, and rich art throughout. This hotel also features two amazing restaurants, one featuring Jamaican cuisine and the other in a New American style. Ideal location, near the Chicago Riverwalk, Chicago Theater, and Millennium Park.

23. Silversmith Hotel – The Loop

Hotel phone: 312.372.7696
Independently-owned, boutique, luxury hotel. Located in Jewelers Row, the hotel matches their décor to their setting with vibrant jewel-tones and Swarovski crystal lamps and tables. Rather than suites, the hotel offers Premium Rooms with an extra seating area and pullout couch. Cozy, glitzy, and fun, this is a perfect getaway for couples. Near the Chicago Riverwalk and Millennium Park.

24. Ivy Boutique Hotel – Streeterville

Hotel phone: 312.335.5444
Stylish, boutique, luxury hotel in the smallest skyscraper in the city. This cozy, little hotel is perfect for couples, with an intimate lounge area and a seasonal rooftop bar. The Ivy offers mostly suites, all with chic and contemporary décor. Stellar location in the Streeterville neighborhood, just steps away from the city’s top dining and shopping on the Magnificent Mile and close to Navy Pier.