SD › Best Places to Stay in Chicago for Couples, Families, First Timers
Updated: September 27, 2022
Our Favorite Hotels in Chicago
The Best Areas to Stay in Chicago
One of the great 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 the most luxurious five-stars to hip hostels. Most options lie in the city center, but more choices are springing up in Chicago’s dynamic outer neighborhoods.
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
- 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 Hotels in Chicago
Chicago Athletic Association • Blackstone • InterContinental Magnificent Mile • Omni Hotel & Suites Magnificent Mile
- Best Budget Hotels in Chicago
Found Hotel River North • HI Chicago Hostel • Freehand
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.
- 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.
- 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.
- 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
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
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 Hotel & Suites 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.
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.
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.
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.
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.
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.
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”.
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) .
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