One of the great American cities, Chicago is crammed with fabulous places to stay, from hip hostels to the most luxurious five-stars. Most options lie in the city center, but more choices are gradually springing up in Chicago’s dynamic outer neighborhoods.
Most of Chicago’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 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”.
While it’s relatively easy to explore the city center on foot, Chicago’s outer neighborhoods cover a vast area, best approached by car, Chicago Transit Authority’s 24hr “L” Train network (transitchicago.com), or Metra trains (Wmetrarail.com). Taxis and Uber/Lyft cars are easily available throughout the city.
• 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).
• If driving, be prepared for overnight parking rates of up to $50 at top hotels in the city center.
The Best Places to Stay in Chicago
Best Luxury Hotels in Chicago
Sofitel Chicago Magnificent Mile • The Peninsula Chicago • The Langham Chicago • Waldorf Astoria Chicago
Best Boutique Hotels in Chicago
Staypineapple • Virgin Hotels Chicago • W Chicago – Lakeshore • Sono Chicago
Best 3-Star/4-Star Hotels in Chicago
ACME Hotel • Found Hotel Chicago • Chicago Athletic Association Hotel • Ace Hotel Chicago
Best Cheap Hotels in Chicago
HI-Chicago – The J. Ira & Nicki Harris Family Hostel • Urban Holiday Lofts • Holiday Jones • Chicago Parthenon Hostel • Chicago Getaway Hostel
Best Neighborhood to Stay for First Timers: 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 (currently 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 Chicago. It’s also home to some of the city’s best hotels, though these tend to be on the pricey side.
Most Romantic Neighborhood: Oak Park
Though it officially lies beyond the city’s western boundary, charming Oak Park has long been part of the greater Chicago urban sprawl, lying some nine miles west of the Loop (it’s around 25 minutes on the Green Line ‘L” train). It’s quiet, leafy streets feature small parks, cozy cafés and a couple of fascinating sights: Ernest Hemingway’s Birthplace Museum (hemingwaybirthplace.com), where the famous author spent his early childhood, and the Frank Lloyd Wright Home and Studio (flwright.org). Wright also designed the nearby Unity Temple, dubbed the “first modern building in the world”. In more recent times couples have taken to locking padlocks (aka ‘love locks’, symbolizing love), along the fence underneath the I-290 viaduct on Oak Park Avenue – the Hemingway Museum sells them. Oak Park is home to some extremely romantic hotels, too – the Carleton of Oak Park Hotel, Harvey House Inn, and elegant Bishops Hall B&B.
For a location closer to the Loop (Downtown), consider Gold Coast, Chicago’s luxury neighborhood on Lake Michigan; picturesque streets, posh boutiques, and high-end restaurants abound, along with some chic hotels (Claridge House, Viceroy Chicago and the Ambassador Chicago). Other than a small beach, there’s not much in the way of specific attractions here, though restaurants such as steak specialist Maple & Ash (www.mapleandash.com), and stylish 3 Arts Club Café (https://rh.com/content/category.jsp?context=Restaurant_CHI) 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 ands clubs in the city. Enjoy the classic tiki bar vibe at Three Dots and a Dash (www.threedotschicago.com), live music at plush cocktail lounge Bassment (www.thebassmentchicago.com), or drinks at TAO Chicago (taochicago.com), an Asian-themed restaurant that morphs into a fashionable nightclub. Cheaper drinks are available at no-frills neighborhood bottle-shop come bar Rossi’s (412 N State St), with proper Guinness served at The Kerryman (ww.thekerrymanchicago.com). House of Blues Chicago (www.houseofblues.com) is also here.
With more time, check out the Oldtown neighborhood, home to comedy club legend The Second City (www.secondcity.com) and hip boutique hotel Sono Chicago, and Pilsen, a lively Latino neighborhood home to famed live venue Thalia Hall (www.thaliahallchicago.com), the Punch House bar (www.punchhousechicago.com) and live piano bar Tack Room (www.tackroomchicago.com).
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 (auchevaldiner.com), Stephanie Izard’s Girl and the Goat (girlandthegoat.com), old-school Italian sandwiches at J.P. Graziano Grocery (jpgraziano.com), classic diner Lou Mitchell’s (www.loumitchells.com) and world-famous cocktail lounge The Aviary (www.theaviary.com). The West Loop is also home to Greektown, crammed with authentic bakeries and restaurants (mainly along South Halstead St). Though there’s not much in the way of attractions (beyond restaurants), staying in West Loop means being within walking distance (or short cab ride) of all the sights in the Loop itself.
Best Neighborhood for Shopping: The Magnificent Mile
The obvious choice – Magnificent Mile 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. Just north of the Loop, it’s also within walking distance of hotels in the West Loop and Streeterville, while the strip itself (actually Michigan Avenue) peters out at the southern end of Gold Coast. On route there are plenty of sights in between the shops, notably the John Hancock Building (360chicago.com) and the Historic Water Tower.
Best Neighborhood for Local Vibe: Wicker Park/Bucktown
Beyond Downtown, Chicago is a vast patchwork of neighborhoods full of local color, with adjacent Wicker Park and Bucktown two of our favorites. Both districts are crammed with vintage stores, hip cafés, a diverse array of restaurants and bars, bookstores, art galleries, and unique shops. 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 (www.subt.net), Davenport’s Piano Bar (www.davenportspianobar.com) and cocktail pioneer Violet Hour (www.theviolethour.com), or head up to the Cabana Club rooftop bar (www.therobey.com/#cabana-club) at The Robey hotel for views across the whole city. In Bucktown we love local bar Map Room (www.maproom.com), and 1920s ice cream parlor Margie’s Candies (1960 N Western Ave). In addition to the Robey, top hotels in the area include Wicker Park Inn, cozy Ray’s Bucktown Bed and Breakfast, and hip budget options Urban Holiday Lofts and Holiday Jones.
Just over two miles northwest of the Loop, on the west side of the Chicago River, both neighborhoods are easily accessible via the Blue Line “L” (7–10 minutes from the Clark/Lake station in the Loop).
Unsafe Areas of Chicago
Central Chicago is generally quite safe, though the usual precautions should be taken at night. South Side Chicago still suffers from high levels of crime and one of the highest murder rates in the US, but there’s no reason to venture here (Hyde Park is fine).
1 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; theskydeck.com), as well as the Theatre District and iconic Chicago Board of Trade. Other major attractions include the world-class Art Institute of Chicago (www.artic.edu), the American Writers Museum (americanwritersmuseum.org), the future location of the Chicago Blues Experience (www.chicagobluesexperience.com), and Chicago River cruises (cruisechicago.com) – cruises are the best way to take in all the amazing architecture. The greenbelt on the lakefront includes Grant Park and Millennium Park with its giant stainless-steel “Cloud Gate” sculpture, known locally as “The Bean”. The Jay Pritzker Pavilion in the park hosts the annual Chicago Blues Festival and Chicago Jazz Festival.
The Best Hotels in the Loop (Downtown Chicago)
Chicago Athletic Association Hotel • Hotel phone: +1 312 940 3552
HI-Chicago – The J. Ira & Nicki Harris Family Hostel • Hotel phone: +1 312 360 0300
Hotel Julian Chicago • Hotel phone: +1 312 346 1200
LondonHouse Chicago • Hotel phone: +1 312 357 1200
Staypineapple • Hotel phone: +1 312 940 7997
Virgin Hotels Chicago • Hotel phone: +1 312 940 4400
theWit Chicago • Hotel phone: +1 312 467 0200
2 The Magnificent Mile & River North
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 Center (with its 360 Chicago observation deck; 360chicago.com). Also here, the Chicago Sports Museum (www.chicagosportsmuseum.com). River North lies on the west side of Mag Mile, now a stylish neighborhood of art galleries, restaurants and nightclubs set in former warehouses. Though it’s best known for nightlife, River North also features theMART (www.themart.com), a converted office building full of design showrooms, Eataly Chicago (www.eataly.com/us_en/stores/chicago), Chicago’s Holy Name Cathedral (www.holynamecathedral.org), and antique-packed Driehaus Museum (driehausmuseum.org).
The Best Hotels in River North/Magnificent Mile
ACME Hotel • Hotel phone: +1 312 894 0800
The Drake • Hotel phone: +1 312 787 2200
Found Hotel Chicago • Hotel phone: +1 224 243 6863
Freehand Chicago • Hotel phone: +1 312 940 3699
The Langham Chicago • Hotel phone: +1 312 923 9988
The Peninsula Chicago • Hotel phone: +1 312 337 2888
Sofitel Chicago Magnificent Mile • Hotel phone: +1 312 324 4000
Waldorf Astoria Chicago • Hotel phone: +1 312 646 1300
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 (mcachicago.org) and family-friendly Navy Pier (navypier.org), 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, Ohio Street Beach.
The Best Hotels in Streeterville
Hotel Audrey • Hotel phone: +1 312 787 6000
Hotel EMC2 • Hotel phone: +1 312 915 0000
Ivy Hotel • Hotel phone: +1 312 335 5444
Loews Chicago Hotel • Hotel phone: +1 312 840 6600
The Ritz-Carlton, Chicago • Hotel phone: +1 312 266 1000
Sheraton Grand Chicago • Hotel phone: +1 312 464 1000
W Chicago – Lakeshore • Hotel phone: +1 312 943 9200
4 The 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. Other attractions in West Loop include Old St. Patrick’s Catholic Church (www.oldstpats.org), monthly Randolph Street Market (www.randolphstreetmarket.com) and the National Hellenic Museum (www.nationalhellenicmuseum.org) in Greektown, also home to Greek restaurants, bakeries and stores.
The Best Hotels in West Loop
Ace Hotel Chicago • Hotel phone: +1 312 764 1919
Chicago Parthenon Hostel • Hotel phone: +1 312 258 1399
The Hoxton, Chicago • Hotel phone: +1 312 761 1700
Hyatt House Chicago/West Loop-Fulton Market • Hotel phone: +1 312 492 0000
Homewood Suites by Hilton Chicago Downtown West Loop • Hotel phone: +1 312 930 0000
Nobu Hotel Chicago • Hotel phone: +1 312 779 8888
5 South Loop:
South Loop is a primarily modern residential neighborhood south of Downtown, its main appeal for families being its proximity to the lakefront Museum Campus comprising the Field Museum of Natural History (www.fieldmuseum.org), Shedd Aquarium (www.sheddaquarium.org) and Adler Planetarium (www.adlerplanetarium.org). It’s also home to Soldier Field (the iconic Chicago Bears stadium; soldierfield.net), legendary Chess Records (open for tours; www.bluesheaven.com/home.html), 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.
The Best Hotels in South Loop
Hampton Inn Chicago McCormick Place • Hotel phone: +1 312 791 1121
Homewood Suites By Hilton Chicago Downtown South Loop • Hotel phone: +1 312 753 3100
Hyatt Regency McCormick Place • Hotel phone: +1 312 567 1234
Marriott Marquis Chicago • Hotel phone: +1 312 824 0500
The Wheeler Mansion • Hotel phone: +1 312 945 2020
6 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; www.alinearestaurant.com). The Chicago History Museum (www.chicagohistory.org) is also here, as well as a couple of family-oriented beaches on Lake Michigan.
The Best Hotels in Lincoln Park
Chicago Getaway Hostel • Hotel phone: +1 773 929 5380
Hotel Versey Days Inn by Wyndham Chicago • Hotel phone: +1 773 525 7010
Hotel Lincoln • Hotel phone: +1 312 254 4700
Villa D’ Citta Bed & Breakfast • Hotel phone: +1 312 771 0696
The Willows • Hotel phone: +1 773 528 8400
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, and excellent restaurants, as well as Legacy Walk (legacyprojectchicago.org), the world’s first outdoor LGBTQ history museum.
The Best Hotels in Boystown
Best Western Plus Hawthorne Terrace Hotel • Hotel phone: +1 773 244 3434
Majestic Hotel • Hotel phone: +1 773 404 3499
Villa Toscana Guesthouse • Hotel phone: +1 773 404 2416
8 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 (www.msichicago.org) is the major highlight here, along with the DuSable Museum of African American History (www.dusablemuseum.org). Hyde Park is just 15 minutes from the Loop via Metra Electric District trains, but its leafy streets and racially diverse population makes staying here a fascinating contrast from Downtown.
The Best Hotels in Hyde Park
Hamlin House B&B • Hotel phone: +1 773 848 7248
Hyatt Place Chicago-South/University Medical Center • Hotel phone: +1 773 752 5300
Sophy Hyde Park • Hotel phone: +1 773 289 1003