Wondering where to stay in Chicago? From Chicago Loop to the Magnificent Mile, discover the neighborhoods with the best restaurants, hotels, bars and attractions in the entire city.
Chicago is a city of irresistible contrasts, with a vibrant pulse to match that of any major American metropolis. Whether you’re a history and art lover, foodie, expert on architecture, sports enthusiast, or shopaholic, Chicago is truly a city that offers an abundance of options for every traveler.
Even the city’s many nicknames, from its earliest origin meaning “onion field” to The White City, Windy City, and Second City, speak volumes about Chicago’s ever-evolving identity.
Set against the backdrop of Lake Michigan, one of America’s 5 Great Lakes, Chicago is a place where old world charm meets the modern world’s marvels.
With first-class museums and eateries, a bustling nightlife culture, and all the outdoor festivals and activities one could ask for, it’s safe to say your stay in Chicago will be anything but dull.
From the many sites around Grant Park, such as the Art Institute of Chicago and Field Museum, to the enticing shops of The Magnificent Mile, here are the 10 best places to explore and stay in Chicago.
10 Best Areas to Stay in Chicago
1. Chicago Loop, best area to stay in Chicago
Presided over by the awe-inspiring Willis Tower, Chicago’s Loop has long held visitors in thrall with its dazzling array of shops, restaurants, theaters, parks and art & architectural wonders.
Grant Park, where the world-famous Art Institute of Chicago is located, as well as where annual events such as Lollapalooza and The Taste of Chicago have historically taken place, is one of the the Loop’s central highlights, with the Buckingham Fountain a photo op dream.
Those who are interested in Chicago’s rich architectural history will want to check out the Chicago Architecture Foundation, with its painstakingly accurate model of the city, while the Chicago Cultural Center offers year-round concerts and exhibitions for the public.
The Adler Planetarium is a must for all ages, while street foodies will find a mouth-watering line-up of food trucks bordering Daley Plaza.
Because the Loop is Chicago’s official “downtown,” there are countless lodging options available, from 4-star hotels to budget hostels. As with any major tourist destination, prices largely depend on the season, but do keep an eye out for special discounts and event prices that are listed exclusively online.
2. West Loop / West Town, best Chicago neighborhood for foddies
Chicago’s former industrial district, the West Loop has since become one of the city’s trendiest and most diverse boroughs. Since the turn of the 20th century immigrants have defined West Town’s culture, with their influence continuing to be celebrated through the many sights, sounds, and tastes of the area.
Arguably Chicago’s dining hotspot thanks to its Restaurant Row, the West Loop boasts an unending assortment of dishes and food items from around the world, with more than its share of pubs and live music venues to satiate any nightlife champion.
The French Market, located just inside the Ogilvie train station, spotlights such fare as Belgian fries, lobster rolls, Hawaiian poke bowls, and all manner of pastries and produce, making it the perfect destination for high-end strolling and sampling.
It’s not just food that’s a major draw in the West Loop, however; the Arcade Emporium at Fulton Market is a gamer’s paradise with its pool and air hockey tables, pinball machines, and arcade games, while Brooklyn Boulders gives you the opportunity to rock climb indoors.
For an especially Big Lebowski-worthy evening, you can head to Punch Bowl Social for bowling and brews.
3. South Loop, where to stay in Chicago for museums
Situated on the lakefront Museum Campus, the South Loop is where you’ll find some of Chicago’s grandest museums, as well as the Jazz Showcase, blues label Chess Records, and Buddy Guy’s Legends.
Here is where established and forthcoming artists alike seek out and showcase new work, with students, locals, and travelers coming together for lively nighttime events.
No stay in Chicago is complete without a walk through the South Loop’s elegant Prairie Avenue District, home of the “Millionaire’s Row” where many of Chicago’s earliest elite set up residence.
Those who partake in a water taxi lake route tour can disembark directly in front of Shedd Aquarium, with the nearby Field Museum an ideal companion for your science-themed outing.
The South Loop’s stunning lakefront views make for some of the best hotel possibilities, although prices can run on the costlier side during peak seasons.
4. River North, great for nightlife
This hip neighborhood on the Near North Side boasts a luxurious selection of boutique shops, bistros, and cocktail bars, with the Merchandise Mart, built in the 1920s as part of the former industrial complex and the world’s largest commercial building, a must-do attraction.
The Navy Pier is a summer highlight, with its adjacent Pier Park offering families a full day’s experience thanks to an IMAX cinema, old fashioned rides, mini golf, and boat tours.
Music lovers will no doubt want to check out the world-famous House of Blues and Museum of Broadcast Communications, while the Museum of Contemporary Art and Chicago Shakespeare Theater are for true Renaissance souls.
This area is one of the best places for nightlife. You will find here some of the best pubs and clubs of the city.
The area’s lovely boutique hotels make for a particularly romantic stay in Chicago.
5. Magnificent Mile, luxury area
True to its name, the Magnificent Mile is where over a century of Chicago’s opulence can be found, from Gilded Age hotels, mansions, and even ballrooms to some of the world’s most sumptuous shopping spots.
Here visitors can gawk at impressive (if not imposing) landmark buildings like the Chicago Water Tower, Tribune Tower, Wrigley Building skyscraper, and John Hancock Center, with the latter featuring a rooftop observation deck and restaurant.
The Richard H. Driehaus Museum is set within a 19th century mansion, and holds the largest collection of Louis Comfort Tiffany pieces, as well as Gilded Era art, fashion, and design collections, with the third-floor ballroom hosting a year-round rotation of lectures, cocktail series, and cultural soirées.
The Newberry Library is an intellectual’s haven, with its well-preserved letters from some of the world’s most famous authors, historic maps, and first edition classic books, all open for public viewing.
While hotels along the Magnificent Mile are preciously priced to say the least, you can still stop by for a fine meal and cocktail at such landmark lodgings as the Blackstone Hotel, where countless U.S. presidents have stayed, as well as the more notorious Al Capone.
6. Old Town, nice area where to stay in Chicago
Settled by German immigrants in 1850, Old Town feels like stepping back in time. With its beautiful Victorian architecture, quiet tree-lined streets, and lively goings-on, Old Town frequently ranks high among must-see areas during a stay in Chicago.
The famous Second City Theater, where such comedic legends as John Belushi, Tina Fey, and Stephen Colbert got their start, is a landmark attraction while the edgier Zanies, whose alumni includes the likes of Aziz Anzari, offers adults-only humor.
Just around the corner from Second City is the Old Town Pour House, which on any given day offers at least 90 beers on tap, while the area’s surrounding shops and eateries leave nothing to be desired on the food aficionado front.
7. Lincoln Park, good area for families
Located on the North Lakeside, Lincoln Park is the largest park in Chicago, and further boasts one of the city’s most affluent neighborhoods. Warmer seasons make for ideal beach-going, while the Lincoln Park Conservatory lets guests explore a paradise of tropical flora & fauna.
The Lincoln Park zoo is a crowd-pleaser for all ages, and the Chicago History Museum offers visitors a special treat in the form of a giant, climbable Chicago-style hot dog.
The Steppenwolf Theater Company, where award-winning stars such as John Malkovich and Gary Sinise honed their acting skills, is still up and running, while the lesser-known but equally worthwhile Theatre on the Lake has its own ongoing roster of shows and events.
And of course, an afternoon in Lincoln Park is its own main attraction, with the park’s lily pond, pavilion, and sprawling green making it the perfect picnic site.
8. Theater District, best Chicago neighborhood for theater aficionados
The bustling hub of Chicago’s Theater District is where some of America’s greatest actors and comedians have cut their teeth, and live theater thespians will no doubt want to take in a show at one of the milestone venues including:
- CIBC Theatre, opened in 1906 as a vaudeville club
- James M. Nederlander Theatre, a decadent cinema also dating back to the early 20th century
- Cadillac Palace Theatre, inspired by Versailles
- The Goodman Theatre, Chicago’s largest and oldest Tony Award-winning non-profit theatre
With so many landmark sites and venues to see, you may want to consider booking a Theater District tour, which will take you through the heart of Chicago’s performance past, as well as offer an insider’s glimpse into some of the country’s most opulent venues and architectural masterpieces.
9. Lakeview, welcoming area to stay in Chicago
The laid-back Lakeview area is perfect for visitors looking for a more local, low-key experience during their stay in Chicago. With casual eateries like the iconic Wiener’s Circle and legendary theaters like The Vic, one could easily make a day (or more) of it in Lakeview.
The busy shopping districts along Broadway offer the best vintage clothing, instrument, and furnishing finds, with additional outdoor markets aplenty.
Music lovers will definitely want to explore the showroom of the Chicago Music Exchange and tour one of the largest vintage guitar collections in the world.
Lakeview’s unpretentious bars and neighborhood restaurants, as well as its many live music and event venues, make it a particularly welcoming area to stay in Chicago. And with Lake Michigan right outside your door, you’ll have instant access to boating, golfing, and picnic hotspots.
10. Airport area
One seldom considers the airport area of any city as little more than a layover wasteland, but Chicago is one of those rare gems that boasts a number of attractions just beyond the terminal.
Foodies will especially delight in tasting famed Chicago fare like deep-dish pizza, as well as Chicago-style hotdogs, at the many eateries located around O’Hare International.
The 48 lanes of Brunswick Zone are an enticing draw for bowling pros, while the Lake Park Golf Course is located just 10 minutes from the airport; both feature a full range of snacks, drinks, and casual entertainment.
Just 5 miles from O’hare, Schiller Woods sits atop an 8,000 acre stretch of forest and wetland, and even contains a natural prairie. Hikers can take full advantage of the many trails, as well as savor the area’s natural wildlife.
Due to the proximity of the CTA Blue Line, which connects O’Hare to the downtown Chicago district, it’s more than feasible to find lodgings just off the airport stretch, which often cost significantly less than more centrally located hotels.
Traveler’s Tip: Know Before You Go
Like all great cities, a stay in Chicago may call for more planning ahead than usual. There are so many sights, events, and areas of interest worth making time for, that you’ll want to lay out an itinerary that allows for maximum ease of transportation and stress-free sightseeing.
Many of Chicago’s biggest attractions and venues offer special discounts, with hotels providing tie-in tours and services for guests on the regular.
For more popular restaurants and shows like the Blue Man Group, it’s advisable to book ahead of time in order to reserve a spot.