5 COOLEST Neighborhoods in Chicago [April 2024!]

5 COOLEST Neighborhoods in Chicago [[date]!] 1

Ah, Chicago; the city of the Cubs, Al Capone, and the musical of the same name. Oh, and of course the home of deep-dish pizza! Those looking to visit the Windy City are in good company, with nearly 58 million people making a beeline there last year.

But with 77 distinct community areas, working out where to stay in this city can be tricky.

That’s why our travel pros have written this insider guide for where to stay in Chicago, so you know the best neighborhood to pick, based on what matters to you!

Planning your accommodation should be stress-free so you can get on with the important stuff, like working out which pizza you’ll be having.

So let’s get to it; by the end of this article, you’ll navigate the city like a pro, knowing exactly where to stay in Chicago!

Table of Contents

Quick tips – Where to stay in Chicago

At A Glance: Where To Stay In CHICAGO

Where to stay in Chicago

Not worried about where you’ll be and just looking for a fit for you? Check out our top picks for Chicago in general!

htjltbl-table__image Best Air BnBBest Air BnBJessica’s Archway Apartment
  • Air conditioning
  • Bedroom comforts
  • Bathroom essentials
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htjltbl-table__image Best Budget HotelBest Budget HotelCarlton Inn Midway
  • Ironing facilities
  • Restaurants
  • BAR
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htjltbl-table__image Best Mid-Range HotelBest Mid-Range HotelVilla D’Citta
  • Elegant accommodation
  • Luggage storage
  • Terrace
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htjltbl-table__image Best Luxury HotelBest Luxury HotelWyndham Grand Chicago Riverfront
  • Private bathroom
  • Air conditioning
  • Restaurant
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Best Air BnB in Chicago – Jessica’s Archway Apartment

Jessica’s Archway Apartment

Jessica’s Archway Apartment is the best Air BnB in Chicago

Unrivaled elegance and unadulterated bliss await you at this historic Chicago Air BnB rental! A former hotel in the 1920s, this property has been renovated to provide lavish and cushy Chicago accommodations. 

Featuring large archways and other original Art Deco elements, this property has been modernized significantly to provide all the creature comforts you need for a chic and cushy stay. 

With 2 bathrooms and 2 bedrooms, it can also accommodate up to 5 guests. And, did I mention that it is located conveniently across the Lincoln Park Zoo and Conservatory?


Best budget hotel overall – Carlton Inn Midway

Carlton Inn Midway

Carlton Inn Midway is the best budget hotel in Chicago

The modern rooms at Carlton Inn Midway feature a flat-screen TV, a private bathroom, and a refrigerator. They provide ironing facilities, a telephone, and tea and coffee making facilities.

A satisfying breakfast is served each morning, and there are numerous restaurants and eateries nearby.


Best mid-range hotel overall – Villa D’Citta

Villa D’Citt

Villa D’Citta is the best mid-range hotel in Chicago

Situated within walking distance of Diversey Railway Station, this comfortable bed and breakfast is an ideal base for those wanting to explore Chicago and its surrounds. It also offers a sun deck and a Jacuzzi.

Villa D’Citta provides elegant accommodation in addition to a library, a concierge, and luggage storage. It also features a garden and a lift.


Best luxury hotel overall – Wyndham Grand Chicago Riverfront

Wyndham Grand Chicago Riverfront

Wyndham Grand Chicago Riverfront is the best luxury hotel in Chicago

Rooms at Wyndham Grand Chicago Riverfront are chic, air-conditioned, and provide wireless internet access.

This hotel features a restaurant and bar where guests can unwind of an evening with dinner and a drink. A choice of cafés and restaurants are also found in the surrounding area.


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Chicago's Neighborhood Guide


Located in the state of Illinois in the US Midwest, Chicago is the giant on the shores of Lake Michigan.

It’s a sprawling city of industry that has hauled itself up from the ashes (literally – a giant fire burned it down in the 19th century) to be what it is today.

Chicago is the third most populous city in the US and the second most visited. It’s not hard to see why when you look at the sheer range of tastes the city caters for.

It’s a foodie heaven, a sporting Mecca, a shopper’s dream, and it’s got more public art than a culture-lover could shake a stick at!

Chicago is almost as famous for its many neighborhoods, each with its own culture and vibe.

There’s Pilsen, where vibrant street art and Hispanic culture have a home, along with the best Mexican food in town. Gold Coast is always a favorite with the crowds, with its sparkling lake setting the scene for the homes – and playgrounds – of the rich and fabulous.

Then again, Ukrainian Village might be more your style, with trendy boutiques next to fancy historic churches. Roscoe Village is perfect for older parents wanting to hunt out some antiques while the younger adults party the night away in Boystown. Or how about Wrigleyville for the sports?

Whatever you’re into, Chicago has an entire area – or two – just for you!

Chicago’s five best neighborhoods to stay in

Neighborhood #1 - The Loop

(Where to stay in Chicago first time)

The Loop

The Loop is our pick for where to stay in Chicago first time

Chicago’s official downtown area, The Loop is perfect for first-timers; you’ll find all you could want on your doorstep. This is the CBD of one of the US’s largest cities, and as such, it’s just as busy, noisy, and exciting as you’d imagine!

The Loop is named after the train line that encircles this area, so it’s easy to get yourself in, around, and out of the city.

West Loop will have your mouth watering, as it is home to many culinary delights – particularly those found in Greektown. It’s also known for its speakeasy bars and other forms of eclectic nightlife.

South Loop is the land of the high-rises and has come a long way from the days when it was known as Satan’s Mile. It’s also made a name as a tourist attraction hotspot, housing aquariums, planetariums, and museums.

While staying in The Loop, you absolutely have to get yourself to Millenium Park, with its iconic Cloud Gate metallic sculpture (hint: to fit in with the locals, just call it ‘The Bean’). It also lies near Lake Michigan, so how about taking a stroll down the riverwalk on your way home from a performance in Chicago’s only official theatre district?

The walk itself is a work of art, having been cleverly designed to allow for free walking, as well as boasting areas to rest and people-watch. The many bars and restaurants along the way help a bit too!

Things to do in the Loop

  • Wander around Millenium Park and snap a pic at Cloud Gate
  • Pay a visit to Alder Planetarium
  • Get cultured at the Art Institute of Chicago
  • Check out the light and music show at Buckingham Fountain
  • Take in a show at Chicago Theatre

Where to Stay in the Loop

Best Air BnB in the Loop – Anne’s Air BnB

Anne’s Air BnB

Anne’s Air BnB is the best Air BnB in the Loop

Traveling on a tight budget? Then, this Chicago Air BnB rental is the right one for you! Located in the exquisite and modern downtown area, this apartment boasts easy and quick access to the must-see attractions in Chicago. 

And, even with its inexpensive price, this shared rental space lets you enjoy a plethora of amenities, including cable TV, kitchen, private bath, reliable Wi-Fi access, and queen-sized bed.


The best budget hotel in The Loop  – Congress Plaza Hotel Chicago

Congress Plaza Hotel Chicago

Congress Plaza Hotel Chicago is the best budget hotel in the Loop

The Congress Plaza Hotel is conveniently located, offering easy access to many of the city’s hotspots. Its rooms provide sweeping views of the city.

Right on the lake, this hotel offers a valet service and fitness center, while the onsite restaurant and bar will help you settle in right away.


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The best mid-range hotel in The Loop – Best Western Grant Park Hotel

Best Western Grant Park Hotel

Best Western Grant Park Hotel is the best mid-range hotel in the Loop

The Best Western Grant Park Hotel offers spacious rooms with a range of cable/satellite channels, heating, and private bathrooms. Onsite facilities include a swimming pool and a fitness center.

The staff, who are available 24 hours, can help you book tickets or tours to anything in the city you might wish.


The best luxury hotel in The Loop –  Gray Hotel Chicago

Gray Hotel Chicago

Gray Hotel Chicago is the best luxury hotel in the Loop

This 4-star hotel within walking distance of much that The Loop has to offer provides a 24-hour reception, valet parking, and babysitting/child services. Additional amenities include a ticket service, a concierge, and luggage storage.

All rooms are air-conditioned and equipped with a mini bar and cable/satellite channels.


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Neighborhood #2 - West Town

(Where to stay in Chicago on a budget)

West Town

West Town is our pick for where to stay in Chicago on a budget

Slightly north-west of the central city, you’ll find West Town, more a cluster of sub-regions than one individual neighborhood. The prices are a touch more manageable for those on a budget, while you’re still in easy reach of everything the rest of the city has to offer.

Wicker Park (more on this later) is a cool area on the northern edge of West Town, and is sure to appeal to the hipster in you. That bohemian flair can also be found in Humboldt Park with its indie bookstores.

In fact, you won’t find any large chain stores on the 1.6 mile stretch of Chicago Avenue running through this region. So, for those not all too keen on globalization, this is the perfect street to take a stroll down and pop in for a look at what the independent traders have in stock.

Ukrainian Village is where you can find amazing ethnic foods and hip nightspots. Settled by Ukrainian and Polish immigrants in the 19th and early 20th century, it has retained the look and feel of its cultural heritage, though is now home to people from all over the world. Keep a look out for the eye-catching churches that dot the area.

Culture is alive and well and living in West Town. There are a number of smaller theatre companies vying with intimate music venues, and a bunch of hip coffee shops waiting to serve them all!

Things to do in West Town

  • Catch a unique event at the stunning Chopin Theatre
  • Have a picnic overlooking the skyline at Eckhart Park
  • See the city from the water with Kayak Chicago
  • Stop in for a musical performance at The Hideout
  • Take a dip in the AIRE ancient baths

Where to Stay in West Town

Best Air BnB in the West Town – Erica and Ryan’s Air BnB

Erica and Ryan’s Air BnB 

Erica and Ryan’s Air BnB  is the best Air BnB in the West Town

Even with its convenient central location, this Air BnB rental is surprisingly laid-back and peaceful. A perfect place to crash after a day of sightseeing in Chicago, this rental is on a serene street that’s just a block away from the famed shops, bars, and restaurants of California Corridor. 

Renovated recently, this house combines its1900 Victorian charm with modern amenities, like air-conditioning and many more.


The best budget hotel in West Town – Holiday Jones

Holiday Jones

Holiday Jones is the best budget hotel in West Town

Holiday Jones has comfortable rooms that are ideal for travelers on a budget. After settling into their room, guests can explore the area by using the Division Subway Station, which is a brief stroll from the hostel.

On-site dining options include a restaurant, which is a convenient spot to have a meal. In the evening, guests can enjoy a drink in the comfortable lounge bar.

The area surrounding Holiday Jones is well-known for its nightlife, with plenty of places to go for a drink or dance.


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The best mid-range hotel in West Town – Wicker Park Inn

Wicker Park Inn

Wicker Park Inn is the best mid-range hotel in West Town

The bed & breakfast’s rooms are spacious and offer a kitchenette equipped with a refrigerator and microwave. All rooms have a private bathroom and wireless internet access.

Wicker Park Inn Chicago is close to Damen Railway Station, making it easy for guests to explore Chicago and its surrounding areas.


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The best luxury hotel in West Town – Ace Hotel Chicago

Ace Hotel Chicago

Ace Hotel Chicago is the best luxury hotel in West Town

Ace Hotel Chicago provides a laundry service and luggage storage.

The hotel, which is called ‘exceptional’ in recent guest reviews, has modern rooms that are accompanied by a range of essential amenities to ensure guests have a comfortable stay.

Those staying at Ace Hotel Chicago can unwind at the on-site bar, suitably based for a drink.


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Neighborhood #3 - River North

(Best area to stay in Chicago for nightlife)

River North

River North is our pick for best area to stay in Chicago for nightlife

River North puts you right in the center of things while giving you a taste of the high-life. You’ve got the world-class shopping of the aptly named ‘Magnificent Mile’ at your doorstep, and it is second only to Manhattan in the quality of the art galleries.

That’s your days sorted, then.

River North is the best-known nightlife area in all of Chicago, having long been a heavyweight in the after-hours entertainment stakes. There is something for everyone here, from comedy clubs to tapas bars; from craft cocktail lounges to country and western joints – and everything in between!

The fine-dining of River North is well known, as you can while away hours, or an entire night, with the many degustation menus about and their matching wines. There’s no better place to lose track of time with friends, family, or your significant other, than amongst the glitz and glam of this district.

Hubbard Street is an icon for visitors and locals alike. Beyond 8 pm, weekday or weekend, on Hubbard Street all bets are off. It’s the perfect place to catch up with friends or go bar-hopping.

People from all walks of life find their way here, so you can find business executives passing the newly minted college crowd on the way to their chosen venues (which usually aren’t the same). So rest assured, whoever you are, you’ll fit right in!

Things to do in River North

  • Shop ‘til you drop on the Magnificent Mile
  • See the city from the air on the giant wheel at Navy Pier
  • Sample the craft beers and arcade games at Headquarters Beercade
  • Attend the rocking Gospel Brunch at the House of Blues
  • Laugh with the local stand-ups at The Comedy Bar

Where to Stay in River North

Best Air BnB in River North – Dean’s Air BnB

Dean’s Air BnB 

Dean’s Air BnB  is the best Air BnB in River North

Channel your inner rock star by staying at this extraordinary Chicago Air BnB rental. Known as a music lover’s paradise and abode, this property is decked out in music as well as rock and roll memorabilia. And, this 2-bedroom apartment features tons of fun touches, such as an antique hi-fi and a wooden carved canopy bed. 

What’s more, its proximity to public transport makes getting anywhere in Chicago a breeze.


The best budget hotel in River North – Hotel Felix

Hotel Felix

Hotel Felix is the best budget hotel in River North

This 4-star hotel makes for an ideal base in Chicago. Guests have called it ‘a prime location in the heart of downtown’ Rooms are air-conditioned, and a Wi-Fi connection is included free of charge.

Hotel Felix features a 24/7 reception, an onsite fitness room, and a wellness center.


The best mid-range hotel in River North – Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North is the best mid-range hotel in River North

This retro designed hotel is surrounded by a variety of restaurants and cafés and is within a 10-minute walk of Merchandise Mart Railway Station.

It’s facilities, alongside its funky decor, include a wellness center, spa, and billiards.


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The best luxury hotel in River North – The Langham Chicago

The Langham Chicago

The Langham Chicago is the best luxury hotel in River North

Rooms at The Langham Chicago are luxurious and air-conditioned, offering a mini bar, wireless internet access, and slippers. They all have a desk, an alarm clock, and heating. The hotel itself also features a sauna, an indoor pool, and a Jacuzzi.

The hotel treats guests to a variety of deluxe amenities, such as a limousine service and Chuan Spa.


Neighborhood #4 - Bucktown

(Coolest place to stay in Chicago)


Bucktown is our pick for the coolest place to stay in Chicago

Street art and long, leisurely brunches; this is, without a doubt, the coolest neighborhood in Chicago, if not the States. Inseparable from its sister village, Wicker Park (see above), the two are actually divided by North Avenue, though similar in the crowds they attract.

Bucktown reportedly got its name from the male goats, or ‘bucks,’ belonging to the Polish immigrants that largely founded the area in the 1800s. Repeated waves of immigration – Jewish in the first half of the 20th century, then Latino after 1960 – have kept this neighborhood alive and thriving.

Now home to artists and musicians who were seeking the lower rents while still in easy reach of downtown, Bucktown is one of the easiest neighborhoods to navigate within and out of to access the rest of the city.

It’s also known, along with Wicker Park, for its nightlife scene, housing eclectic combinations of bars, pubs, and clubs. Earlier in the day, however, you see scores of young people exiting brunch spots, merry from the midday drinks and ready to move to the next hip venue.

To explore this uber-cool neighborhood, you’ll want to stride the length of either Damen, Milwaukee, or North Street, each with their own calling cards and all just as engaging. The architecture, like most of Chicago, is also worth a look. One of our picks, The Robey, is known for its Art Deco design.

Only 15 minutes from downtown, Bucktown deserves its current 15 minutes of fame as the coolest spot to be in Chicago!

Things to do in Bucktown

  • Learn to play the made-up bumper car game at WhirlyBall
  • Discover new talent at Corbett vs. Dempsey Art Gallery
  • Wander along the abandoned rail tracks of The 606
  • Find yourself a one-of-a-kind treasure at the ‘gram worthy Asrai Garden
  • Sample the tasty goods at the Hoosier Mama Pie Company

Where to Stay in Bucktown

Best Air BnB in Bucktown – Arlete’s Air BnB

Arlete’s Air BnB 

Arlete’s Air BnB  is the best Air BnB in Bucktown

No list of the best Chicago Air BnB rentals is complete without the inclusion of Arlete’s flat. Located in Bucktown’s peaceful tree-lined streets, this rental offers instant access to Holstein Park, Logan Square, Wicker Park, and Senior Citizens Park. 

Great for all types of travelers, this flat has been updated recently with hardwood floors, new bathroom, and kitchen.


The best budget accommodation in Bucktown – Ray’s Bucktown Bed and Breakfast

Ray’s Bucktown Bed and Breakfast

Ray’s Bucktown Bed and Breakfast is the best budget accommodation in Bucktown

Ray’s Bucktown Bed and Breakfast (with a whopping 9.9 rating from hundreds of reviews online) has rooms that are equipped with everything you might need to ensure an enjoyable stay.

Those wishing to have a meal nearby needn’t look any further than Ray’s on-site restaurant, which is available every day for breakfast.


The best mid-range accommodation in Bucktown – The Hotel at Midtown

The Hotel at Midtown

The Hotel at Midtown is the best mid-range accommodation in Bucktown

There are a range of facilities available for those staying at this hotel, including a limousine service and laundry service – not to mention the swimming pool exclusively for guest use.

The rooms are air-conditioned and include a refrigerator, a laptop safe, and tea and coffee making facilities. Bathrobes are also included for comfort.


The best luxury accommodation in Bucktown – The Robey

The Robey

The Robey is the best luxury accommodation in Bucktown

Located in an iconic art-deco building that dominates the skyline for miles around, staying in The Robey is a cultural experience.

The Robey’s rooms are fitted with all the essentials to ensure a comfortable stay.  There’s also an outdoor pool for guest use.

Those staying at this 4-star property can wake up to a satisfying breakfast served each morning before heading out from the hotel to explore the local region.


Neighborhood #5 - Lincoln Park

(Best neighborhood in Chicago for families)

Lincoln Park

Lincoln Park is our pick for coolest place to stay in Chicago

Not the band from the late nineties but the neighborhood in Chicago, Lincoln Park is the ideal blend of all a family could want when visiting a big city. Currently the most fashionable place to live in the city, it’s high end, but also very family-friendly.

It has become very popular with 20-something and 30-something crowds looking to start families. The area is known for its schools; this is great for the locals, and also offers visitors a sense of safety in a big and unknown city.

Lincoln Park is well-connected, meaning you are never far away from the major tourist spots in the CBD if you wish, but you also have the quieter, leafier areas to hang in.

Named for the largest park in Chicago that resides right there, it is also home to a large number of University students. These facts combined mean plentiful facilities for energetic youngsters. You can hike a bunch of trails, go cycling, or picnic in the vast green areas that populate Lincoln Park. On the eastern side is North Avenue beach, skirting the edge of Lake Michigan, for those warmer days.

Each of the residential areas has its own shopping hub, so there’s no single great thoroughfare. This is perfect for families who like to get to know their own corner of a city without having to rely on Google Maps just to find the nearest supermarket.

For the kids (and adults) there is Lincoln Park Zoo. This 35-acre attraction is home to over 1200 animals, and it’s free! It’s very walkable, so you can cover a lot of ground before young legs get tired.

Things to do in Lincoln Park

  • Marvel at the creatures at the Lincoln Park Zoo
  • Check out the exciting exhibits at DePaul Art Museum
  • Hike or bike the trails in Lincoln Park
  • Climb the statues and structures with Dorothy and the Tinman at Oz Park
  • Get hands-on with the interactive displays at The Peggy Notebaert  Nature Museum

Where to Stay in Lincoln Park

Best Air BnB in Lincoln Park – Jessica’s Air BnB

Jessica’s Air BnB 

Jessica’s Air BnB  is the best Air BnB in Lincoln Park

Traveling with a group? With 4 beds and 2 spacious bedrooms, this Air BnB rental is perfect for those who are traveling in a group of 8 or less.

Additionally, it only takes a short stroll to Lincoln Park Zoo and Conservatory from the loft. For foodies, the loft is surrounded by a plethora of excellent restaurants. 


The best budget hotel in Lincoln Park – The Willows Hotel

The Willows Hotel

The Willows Hotel is the best budget hotel in Lincoln Park

Each room is set out like a French country manor house, with all the necessary bells and whistles to provide a comfortable stopover.

This hotel is also close to Wrigley Field, so ideally located for the sports fans!


The best mid-range hotel in Lincoln Park – Hotel Versey Days Inn

Hotel Versey Days Inn

Hotel Versey Days Inn is the best mid-range hotel in Lincoln Park

The rooms here are decorated in a funky, pop-culture style with references to Chicago icons and sports. The hotel is close to the Lincoln Park Zoo.

Hotel Versey Days Inn Chicago has modern rooms that are fitted with all the necessities to ensure a pleasant stay. Hot drinks can be made with the provided tea and coffee supplies.


The best luxury accommodation in Lincoln Park – Old Town Lincoln Park Apartment

 Old Town Lincoln Park Apartment

Old Town Lincoln Park Apartment is the best luxury accommodation in Lincoln Park

An apartment rather than a hotel, this accommodation is perfectly suited to a family trip. With two bedrooms and a large lounge room,  there is space for everyone.

With TV, dining table, and kitchen, the family can eat in, or take a bit longer over breakfast when starting the day.


A final word…

Chicago is a city with a bewildering array of neighborhoods, each with its own distinct flavor. Thanks to our guide, you’ll now be able to suss your stay like a local. Why not venture further afield once you’ve found your base through us? You might find a favorite new neighborhood to tell us about.

You’ll never get bored in this city by the lake. From sports and food to culture and music, there is truly something for everyone here!

Staying in our best overall hotel, The Robey, will see you stepping into history and taking a spot in Chicago’s skyline. Its iconic design and industrial beams capture the spirit of the city and the rugged entrepreneurs who built it.

That caps off our experienced travel team’s thoughts and recommendations on where to stay in Chicago. Oh, and make sure you get a selfie in front of The Bean!

“I adore Chicago. It is the pulse of America.” – Sarah Bernhardt

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About the Author Nicola Smart

Gin lover. Coffee addict. Nicola has traveled the world for 7 years and is a staff writer for Hotel Jules. Born in London, Nicola first got the taste of travel studying abroad in Barcelona. Since then she's been hooked - traveling the world non-stop. Passionate about green travel and vegan lifestyle, Nicola spends more of her free time staring at maps wondering where she will head to next!