Planning a trip to the Windy City and in search of the best places to stay in Chicago? Well, you’ve come to the right place! Read on for a detailed look at accommodations in Chicago, from the downtown Magnificent Mile up to Lincoln Park and all points in between.
There are plenty of reasons to travel to the third biggest city in the US. Chicago is a fantastic destination whether you’re into sports, art, history, food, architecture, music, or nightlife.
When deciding on the best areas to stay in Chicago, you’ll want to consider how you want to spend your time there. As with any big city, each area has its own vibe. Wrigleyville is great for catching a Cubs game and partying it up, while River North is a solid choice for exploring the city’s most famous attractions.
If you’re searching for where to stay in Chicago, this guide is for you. We’ll take a look at some of the best neighborhoods in the Windy City and provide recommendations to suit every budget.
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When it comes to the best places to stay in Chicago, it’s hard to top the Loop. This neighborhood truly is the heart of the city and the perfect spot for first-timers.
Staying in the Loop puts you in an ideal location for sightseeing. Here you’ll find some of the city’s most iconic sights, including the Willis Tower and Millenium Park. You’ll save time and money on transportation by staying here as you’ll be able to walk most places.
Fun fact—the Loop is the 2nd largest commercial district in the US after Midtown Manhattan. The amount of hotels, shops, restaurants, theaters, and bars is staggering, giving you nearly endless options for your Chicago visit.
The Loop is actually big enough to be split into a few areas. The central part is bordered by Lake Michigan to the east and the river to the north and west. Once you get south of Grant Park, you’re in what’s known as the South Loop. Cross over the river headed west, and you’re in—you guessed it—the West Loop.
It doesn’t really matter which part of the Loop you choose. Many of the best hotels to stay in Chicago are located in the area, and it’s easy enough to get around no matter where you end up. Here are a few of the best options for accommodations in Chicago that are in the Loop.
Accommodation Options in the Loop
Budget—HI Chicago Hostel: If you’re traveling on a budget but still want to stay downtown, this is the place for you. Relax in the comfortable lounge or meet fellow travelers over a game of pool or ping pong in between all the sightseeing.
Mid-Range—Congress Plaza: It’s hard to top the location of this hotel, just steps away from the scenic Buckingham Fountain in Grant Park. It’s actually not much more expensive to get a room here than the hostel if you prefer a more private option for your Chicago accommodations.
Luxury—Alegra Royal Sonesta: This stylish Art Deco hotel in the Loop has well-appointed rooms. After a big day of exploring, you can enjoy dinner in a classy Italian restaurant and drinks at the retro bar.
River North/Magnificent Mile
Moving on with the best areas to stay in Chicago, River North is a very popular choice. Staying here makes it easy to enjoy all that the Chicago River has to offer, from architecture boat cruises to kayaking.
In this area just north of downtown, you’ll also find the Magnificent Mile. This is the place to shop til you drop as it’s full of high-end department stores and boutiques. Some of the best hotels to stay in Chicago are also located here.
Just a few blocks away is Navy Pier, one of the most fun places to visit in the Windy City. Take a spin on the Ferris wheel here for some amazing views of Lake Michigan and the city’s iconic skyline.
Another reason this is considered one of the best places to stay in Chicago is because of the many culinary and nightlife options. You’ll find just about every type of restaurant and bar imaginable in this part of the city.
Accommodation Options in the Magnificent Mile
Budget—FOUND Hotel: For the location, this place is a fantastic deal. They have both shared and private rooms and offer a discount for extended stays.
Mid-Range—Embassy Suites: There’s a lot to love about this place. This includes the free made-to-order breakfast and the evening reception with complimentary drinks.
Luxury—Peninsula: Stay in the lap of luxury in this 5-star hotel that’s among the best accommodations in Chicago. It has been named the top hotel in Chicago and #3 in the country by US News and World Report.
For those who prefer a more local side to travel, Lincoln Park makes an excellent choice. This neighborhood is one of the nicest in Chicago, and it’s a quick trip on public transportation to get downtown. Lincoln Park offers some of the best places to stay in Chicago.
The main draw of staying here is the massive park after which the neighborhood is named. It’s home to a free zoo, a conservatory, and a long stretch of beach along the shores of Lake Michigan. This is definitely the place to be on a nice summer day in Chicago.
Lincoln Park is the home of DePaul University and has a college-town vibe. That means plenty of options for places to scarf down some of the city’s famous deep-dish pizza and Chicago-style hot dogs!
For a quintessential Chi-town experience, grab a late-night dog at the Wiener’s Circle. They’re especially good after having adult beverages in one of the area’s many bars.
Accommodation Options in Lincoln Park
Here are some of the top options for where to stay in Chicago’s Lincoln Park neighborhood.
Budget—Chicago Getaway Hostel: This fun hostel features both shared and private rooms and is located right in the heart of Lincoln Park.
Mid-Range—Hotel Versey: In the mid-range category, this cool spot describes itself as “where hip meets historic.” A perk of staying here is being able to use the gym next door free of charge.
Luxury—Villa D’Citta: Staying in this “boutique mansion” is definitely a unique experience. Priding itself on its old-world style, this B&B is packed full of hotel-like amenities.
Old Town/Gold Coast
Those seeking to class it up will want to skip the dive bars and hot dog joints and look to the ritzy Gold Coast area just south of Lincoln Park. Here you’ll find high-end hotels with panoramic views of the lake, and they’re some of the best places to stay in Chicago. The area also offers plenty of upscale dining choices.
While the Gold Coast area is just a few blocks, there’s a larger, more interesting neighborhood just to the west in Old Town. It has a history dating back to 1850 with a wave of German immigrants. It’s famous for its Victorian-era architecture.
One of the coolest things about staying in this ‘hood is that it’s home to the Second City—an iconic comedy club. This place helped launch the careers of comedians like Chris Farley, Tina Fey, and Bill Murray. Be sure to add a show here to your list of things to do in Chicago!
Accommodation Options in the Gold Coast
Budget—Claridge House: It’s hard to top this chic hotel for the price in the area. You’ll feel right at home here in the heart of this local neighborhood.
Mid-Range—Whitehall Hotel: This historic hotel was one of the first luxury high-rises in the city. It’s hosted famous guests over the years like Katherine Hepburn and Mick Jagger.
Luxury—Thompson: This boutique 4-star hotel is a great place to rest your head in the Gold Coast area. If you really want to splurge, book one of their epic bi-level suites with a lake view.
Top Things to do in Chicago
There are so many fun things to do in Chicago. You’ll have to make several trips to the city to do them all. Here’s a list of some of the best to get you started.
- Willis Tower: Go to the top of this iconic skyscraper for amazing views of the lake and city.
- Field Museum: This is one of the top museums in the country to visit, and you can easily spend a whole day here.
- Millennium Park: A stroll around this lakefront park is a must when visiting the Windy City, especially for a photo opp with “the Bean.”
- River Cruise: Enjoy the scenery of Chicago’s famous skyline as you cruise along the river.
- Catch a game: This is a sports city, so go and root for the home team. It doesn’t matter whether it’s the Cubs, Sox, Bears, Bulls, Blackhawks, or Fire.
- Eat local specialties: Grab a Chicago-style hot dog and a deep-dish pizza.
For more, be sure to check out this detailed guide on how to spend a weekend in Chicago.
How to Get to Chicago
Most visitors arrive in Chicago at one of the city’s two airports. O’Hare (ORD) is the bigger of the two, offering more flight options. Midway (MDW) is primarily a hub for Southwest.
Both airports are connected to the city by the elevated rail system known as the “L.” The blue line serves O’Hare while the orange line goes to Midway. It takes about 45 minutes to get from either airport to the Loop.
You can also get to Chicago by train from several cities. Trains arrive at Union Station downtown, which is just a few blocks from the Willis Tower. Check Amtrak for schedules and fares.
Several bus companies have routes to Chicago as well, including Greyhound and Megabus. Be sure to book tickets in advance for the best deal.
Should you choose to drive to Chicago, you will have a difficult time finding parking and it’s expensive. You really don’t need a car in this city as there’s great public transportation. In fact, you’ll have a more enjoyable trip without one!
How to Get Around Chicago
Your best bet for getting around Chicago is grabbing a Ventra pass when you arrive. There are 1, 3, and 7-day unlimited ride passes available for $10, $20, and $28 respectively.
These passes are good for all of the bus and train lines run by the CTA. The train system is known as the “L” because many tracks are “el”-evated. The L will get you just about anywhere you want to go in the city, so you probably won’t need to figure out the bus system.
If you’re staying in the Loop or River North, you can easily walk to most of the major attractions in the city. There’s also the Divvy bike share program, where you can take a single trip for just over $3 or get a day pass for $15.
For when you don’t feel like hoofing it, pedaling, or taking public transport, you can always hail a cab. Rideshare apps like Lyft and Uber are also readily available in Chicago.
When to Visit Chicago
Unless you enjoy painfully cold weather with stinging winds, it’s best to skip out on winter in Chicago. Sure, you can find plenty of fun things to do indoors, but many parts of the city aren’t that enjoyable in winter.
Summer in Chitown is a very exciting time with lots of events going on like Lollapalooza and Taste of Chicago. That being said, it can be more crowded and expensive on these popular weekends.
Alternatively, both spring and fall are excellent choices if you want to experience the best of the Windy City. Then you can enjoy it in pleasant weather without the crowds.
Recap of the Best Places to Stay in Chicago
That about wraps it up for this guide on the best places to stay in Chicago. Whether you choose to base yourself downtown in the Loop, along the Magnificent Mile, or up in Lincoln Park, you’re sure to have a great time exploring the Windy City.
There’s so much going on in Chicago that you’ll likely be planning a return visit before you leave. Go ahead and check out a different neighborhood next time so you can experience different sides of the city.
I’ve been going to Chicago for nearly 30 years now and always discover something different when I go. It’s one of my favorite cities in the country, and I hope you end up falling in love with it as well!
This is a post written by contributor, Sasha. He is a teacher, writer, and video producer from Detroit, Michigan. He graduated from Michigan State (Go Green!) and has since lived in China, Indonesia, Mexico, and Colombia. Sasha and his wife Rachel run Grateful Gypsies, where they write about teaching ESL, digital nomad life, long-term travel, live music, and more.
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