Chicago is one of America’s coolest cities. A legendary sports town, a world-class food scene, and some of the most iconic architecture in the USA – simply put, this epic city should be firmly on your bucket list.

From its vibrant music scene, jaw-dropping architecture and DELICIOUS food, the city of Chicago is a culturalist’s playground. You need to try the city’s deep-dish pizza, you can thank me later.

You may even be lucky to see a bull or two around town. Animals in the city, I hear you say?! No, not the animals! The players from the iconic Chicago Bulls basketball team. If you’re lucky, you could even catch a game while you’re in town. 

That said, it’s a massive city and deciding where to stay in Chicago can be incredibly overwhelming. After a few months in this epic city, I have written this guide which takes a detailed look at the best areas of Chicago. My aim is to make your decision-making on where to stay a hell of a lot easier. 

Whether you’re looking to see the top sights, dance the night away or dine on some deep-dish pizza – you’ve come to the right place! This insider’s guide to where to stay in Chicago will get you exactly where you need to go.

So, let’s get to it…

The Bean statue in Millennium Park, Chicago
Cool beans.

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Where Is the Best Place to Stay in Chicago?

So, you’re backpacking in Chicago? You lucky thing! There are loads of cool areas to explore and stay in Chicago. However, deciding which is best for you can be a tricky task.

If you keep scrollin’, I’m going to deep dive into my top five areas and what makes each so great. But if you are a little short on time, don’t worry. I’m going to let you know my top picks for the best hotel, hostel and Airbnb in the city.

The Langham | Best Hotel in Chicago

Corner modern hotel room in The Langham hotel, Chicago

The Langham is the best hotel in Chicago with its unbeatable downtown location and high-end luxuries. On-site you’ll find a spa, pool, and restaurant you can enjoy before or after embarking on your Chicago itinerary.

The Langham will make you feel like royalty with its luxurious room design and stunning common spaces. You’ll soon see why it’s the very best out of all Chicago hotels. Do yourself a favour and lock in this slice of luxury in the big city.

Freehand Chicago | Best Hostel in Chicago

Freehand Chicago

Set in stunning River North is Freehand – which is undoubtedly the best hostel in Chicago. This charming hostel is located inside a classic 1920s building and comes complete with stylish décor.

It has an on-site cocktail bar, a fitness centre, and laundry facilities. Chill out in comfortable common spaces and meet travel buddies to explore the city with. It’s a backpacker’s dream.

Studio With Private Hot Tub | Best Airbnb in Chicago

Studio With Private Hot Tub Airbnb in Chicago

This bright, modern, and clean Chicago studio not only has a lovely interior but also features an incredible outdoor hot tub! You’ll be able to come back and relax after a long day enjoying all the best things to do in Chicago.

Located in a safe area to stay in Chicago near Wicker Park, this top Chicago Airbnb is filled with natural light and has a functional kitchen in case you want to do any cooking. You’ll be hard-pressed to find an Airbnb in the Windy City that can match its value.

Chicago Neighborhood Guide – Places to Stay in Chicago


Downtown/The Loop

Downtown/The Loop is undoubtedly the most famous neighbourhood and the best area to stay in Chicago for first-timers. Home to the city’s business district, this area of Chicago is packed with skyscrapers, lively theatres, and picturesque architectural landmarks.

Streeterville, Chicago


Tucked between Lake Michigan and Chicago’s glitzy and glamorous Magnificent Mile is the lively neighbourhood of Streeterville. It’s one of the best places to stay in Chicago if you’re on a budget.

River North

River North

To the west of Streeterville and the Magnificent Mile is River North. Well known for its art galleries, museums and boutique shopping, River North is also the epicentre for nightlife in Chicago.

Wicker Park

Wicker Park

The coolest neighbourhood in Chicago is undoubtedly Wicker Park. The city’s premier hipster haven, Wicker Park has a great mix of local boutique, innovative restaurants, and upscale doughnut shops and taco stands.


Lincoln Park

Chicago’s Lincoln Park neighbourhood is where everyone from collegiate freshman and newbie lawyers mixes and mingles with young families and well-established brokers. It’s one of the best area to stay in Chicago forfamilies and is where you can enjoy a true slice of the local life.

Chicago is the largest city in the Midwest1 and is a central hub for arts and entertainment, music, food, and culture. It’s one of the best cities you can visit while exploring the USA, so as you can imagine, deciding where to stay can seem daunting at first. You want to get this right!

I get it–now let’s begin with Chicago’s most famous neighborhood: Downtown/The Loop. Located at the center of the city, this part of Chicago is bursting with history and culture, landmarks, restaurants, and bars. You’ll also find iconic spaces like Grant Park which is perfect for a summer picnic. Keep in mind that the Chicago Loop is made up of several sections including the West Loop, where you’ll find some seriously delicious eats and admirable architecture.

North of Downtown are Streeterville and River North. Two of the city’s trendiest neighborhoods, both are great spots for sampling infamous Chicago foods and enjoying exciting nights out on the town.

Chicago sunset aerial view
Just Chicago things – a lake masquerading as an ocean.

Meanwhile, Wicker Park, west of Downtown, is the coolest neighborhood to stay in Chicago with hip bars, chic restaurants, and a slew of independent boutiques.

Further north of Downtown is Lincoln Park. Situated on the shores of Lake Michigan, Lincoln Park is one of the lushest places in Chicago with more than 1,200 acres of green space2. There is also the Lincoln Park Zoo, many museums, and other kid-friendly activities.

If you’re still not sure where to stay in Chicago, fear not. Let’s dive deep into each neighborhood!

Get Your ESTA Before Visiting The US

You should know that most visitors to the US need some form of Visa to enter the country. Fortunately, many passport holders are entitled to apply using the simple and easy to use ESTA Visa scheme which is basically, a cheap, fast electronic Visa.

5 Best Neighborhoods to Stay in Chicago

Navigating the massive city of Chicago is easy thanks to its robust transit system. The city has an expansive network of buses and trains that are efficient, safe, and relatively cheap. There’s really no better way to see the city!

Now, let’s take an in-depth look at the five best neighborhoods in Chicago.

1. Downtown/The Loop – Best Place to Stay in Chicago for First-Timers

Downtown/The Loop is undoubtedly the most famous neighborhood in Chicago. Home to the city’s business district, this area of Chicago is packed with skyscrapers, lively theatres, and picturesque architectural landmarks. Millennium Park is a must-visit if just to take a photo with its world-famous statue: The Bean.

The Bean statue at night
The iconic Bean at night.

It’s also dotted with incredible restaurants where you can sample some of the city’s most delicious foods – yup, we’re talking about Chicago deep-dish pizza and hot dogs. The best of the best is all right here. Head to West Loop to experience some of the best of what Chicago has to offer.

As it’s designed in a grid pattern, navigating Downtown Chicago couldn’t be easier – even if you aren’t the best with a map. You’ll love wandering the city streets and immersing yourself in Chicago’s rich history and diverse culture.

Prefer public transit? The Loop isn’t just a name – it refers to the rail that forms the hub of Chicago’s elevated train system.

If you’re wondering where to stay in Chicago without a car, this is it. It’s the best area to stay in Chicago without a car as you’ll be able to get virtually anywhere in the city from The Loop!

Central Loop Hotel | Best Hotel in Downtown/The Loop

Stylish one-bed room in The Central Loop Hotel, downtown Chicago

The Central Loop Hotel has stylish décor, and spacious rooms and is centrally located in Downtown Chicago. It has a modern lounge bar, concierge service, and a convenient 24-hour reception. Each room is air-conditioned and comes with coffee/tea facilities and on-demand movies. It’s also near to all essential Chicago tourist destinations – so you can pack your days with on-foot explorations!

HI Chicago | Best Hostel in Downtown/The Loop

Common area at HI Chicago hostel

At HI Chicago, you’ll have all of the city’s top tourist attractions, art galleries, museums, shops, and restaurants right at your doorstep. This hostel is massive and comes complete with more than 500 comfortable beds. It’s the perfect place to relax after a long day out in Chi-Town, get remote work done, or make new friends!

Spacious 2 Bedroom Apartment | Best Airbnb in Downtown/The Loop

Spacious 2 Bedroom Apartment in Downtown Chicago

This iconic Airbnb is just steps away from some of Chicago’s best places to visit. Aside from being spotless, comfy, and roomy, you’ll have close convenience of Chicago’s public transportation in case you want to venture to other parts of the city.

This two-bedroom rental also includes high-speed Wi-iFi, a nice TV lounge, and exceptional access to Chicago’s best eats and sights.

Things to See and Do in Downtown/The Loop

  1. Admire architecture from the Chicago River.
  2. Explore the Field Museum.
  3. Enjoy a picnic at Grant Park.
  4. Head to West Loop for some seriously delicious food and stunning architecture.
  5. Get spooked on a Gangsters and Ghosts walking tour.
  6. Stand at the centre of Millennium Park.
  7. See incredible works of art at the Art Institute of Chicago.
  8. Climb to the 99th floor of Willis Tower and enjoy sweeping views out over the city.
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2. Streeterville – Best Place to Stay in Chicago on a Budget

Tucked between Lake Michigan and Chicago’s glitzy and glamorous Magnificent Mile is the lively neighborhood of Streeterville – also one of the best places to stay if money is tight.

View of Streeterville, Chicago from the water
Streeterville might just be one of the most fun places in Chicago!

One of Streeterville’s most famous and fun attractions is the Navy Pier. A bright and vibrant hub for excitement and entertainment for over 100 years now. Navy Pier consists of shops, parks, restaurants, thrilling rides, and lively games.

Whether you want to fly through the air and take a spin on a carousel or navigate your way through Chicago’s Funhouse Maze, there’s something for everyone at Navy Pier.

Not only is Streeterville my pick for fun and games, but it’s also the place to stay on a budget thanks to its great hostel options. There are also some motels in Chicago worth checking out.

If you want to see how the other half live, head to the neighboring town, Gold Coast. Here you’ll find the glitz and the glam. It’s easily one of the more expensive areas of Chicago. It’s a luxury lover’s haven, right on the beach.

Note that you can save even more money if you avoid visiting Chicago on the weekend.

Hotel EMC2 | Best Hotel in Streeterville

Modern hotel room design in Hotel EMC2, Streeterville, Chicago

This incredible place to stay in Chicago boasts some truly epic modern architecture and is within walking distance of Oak Street Beach. You can dine at The Albert, a delicious on-site restaurant that really takes modern design to the next level.

The hotel is also super close to a plethora of other restaurants and shops that you might want to include in your Chicago weekend plans.

Freehand Chicago | Best Hostel in Streeterville

Freehand Chicago

Set just next door, in the neighboring area of River North, is Freehand Chicago. This charming hostel is built in a classic 1920s building and comes complete with stylish décor. It’s got a super cool vibe and is in a cool part of town.

It has a cocktail bar, a fitness centre, and laundry facilities on-site. You can expect lockers and towels to be provided to make your stay extra comfy!

Elegant Suite in Gold Coast | Best Airbnb in Streeterville

Elegant Suite in Gold Coast

This gorgeous Streeterville suite is one of the best Airbnbs in all of Chicago. From its elegant interior and laid-back luxury design, this is an ideal place to stay for couples, digital nomads, or anyone in between!

The suite is ideally designed for up to two guests and is just steps away from the Magnificent Mile and the high-end boutiques of Oak and Rush Street. You’ll be perfectly situated for many of the best things to do in Chicago.

Things to See and Do in Streeterville

  1. Ride the Ferris wheel at Navy Pier.
  2. Join a Chicago Lakefront Neighborhoods Bike Tour.
  3. Get creative at the Museum of Contemporary Art.
  4. Swim at Ohio Street Beach.
  5. If you’re travelling with little ones, head to the Chicago Children’s Museum.
  6. Shop till you drop on Magnificent Mile.
  7. Check out Gold Coast, the neighboring luxury, beach town.

3. River North – Best Place to Stay in Chicago for Nightlife

To the west of Streeterville and the Magnificent Mile is River North. Well known for its art galleries, museums, and boutique shopping, River North is also the epicenter for nightlife making it one of the best areas in Chicago to stay for those who want to party.

Nighttime view of the Chicago River
The Chicago River is an absolute stunner.

Sprinkled throughout this lively neighborhood is a great selection of bars, clubs, and pubs. It’s where you can dance the night away under the stars, listen to great live music below the streets, or rub elbows with Chicago’s elite.

But that’s not all – River North is also home to a mouth-watering array of restaurants. Offering up everything from traditional American fare to fashionable fusions. Your taste buds will be amazed by all the culinary adventures in this area!

Hampton Inn & Suites Chicago-Downtown | Best Hotel in River North

Hampton Inn & Suites Chicago-Downtown

Cool and comfortable, stylish and modern. These are just a few of the reasons The Hampton Inn & Suites is one of my top picks for where to stay in Chicago.

Not only is this hotel close to transit lines, but there are also plenty of bars, clubs, and pubs nearby. It has comfortable rooms, clean facilities, and friendly staff members. Plus, they do a bangin’ breakfast! It’s got to be one of the best Chicago hotels.

Freehand Chicago | Best Hostel in River North

Freehand Chicago

Set in stunning River North is Freehand, this charming hostel is located inside a classic 1920s building and comes complete with stylish décor. It has an on-site cocktail bar, a fitness centre, and laundry facilities. Chill out in comfortable common spaces and find friends to explore the city with!

Cosy River North Studio | Best Airbnb in River North

Cozy one bedroom at Cozy River North Studio with views of Chicago's skyscrapers

Nothing’s worse than having to share a room with others while suffering from a previous night out. Cure your hangover privately in this stunning Airbnb, located right in the famous River North neighborhood.

You’ll be living on a higher floor, meaning that no loud street noises are interrupting your recovery sleep. There’s a Smart TV, high-speed W-Fi, and a fully equipped kitchen ready to be used. On top of that, there’s also a Whole Foods grocery store on-site.

Things to See and Do in River North

  1. Relax at Three Dots and a Dash Tiki Bar.
  2. Join the prohibition speakeasy tour and sip your way around town.
  3. Get your jam on at the Chicago House of Blues.
  4. Jump on a water taxi and explore the town from the water.
  5. Check out the hot spot that is the Navy Pier.
  6. Head to a show at the famous Lookingglass Theatre.
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4. Wicker Park – Coolest Neighborhood in Chicago

One of the coolest neighborhoods to stay in Chicago is undoubtedly Wicker Park. This is the city’s premier hipster haven and has a great mix of local boutiques, innovative restaurants, upscale doughnut shops, and taco stands.

Wicker Park row of houses

Music fans will adore staying here. This dynamic district is where you’ll find some of the city’s most famous live music venues, like the Empty Bottle. Up-and-comers, big names, and superstar artists have all been known to play shows in this neck of the woods.

Wicker Park is also a mecca for shoppers interested in eclectic wares and alternative fashions. Located along the Indie Magnificent Mile, fashionistas can find everything from cutting-edge boutiques and vintage shops to national brands and high-street stores.

The Robey | Best Hotel in Wicker Park

Black and white one bed hotel room in The Robey, Chicago

Located in the heart of Chicago’s Wicker Park neighborhood, The Robey has absolutely everything you need for a convenient and comfortable stay. You’ll be close to some great restaurants and attractions and can also take advantage of the hotel’s on-site bar and cafe.

Public transport is within walking distance so you can easily reach other parts of Chicago. The Robey also boasts an incredible rooftop bar during summer where you can catch an incredible sunset. It’s easily one of the best Chicago hotels – especially in the summer!

Wicker Park Inn | Best B&B in Wicker Park

Wicker Park Inn

This B&B is a perfect option for those looking to be close to some of Chicago’s main attractions. Including the Magnificant Mile and Millennium Park. You won’t be short of activities if you stay here.

As you’d guess by the fact it’s a B&B, you get a FREE daily breakfast. And, the question you all want to know is, what is it like? I can confirm it is delish. Croissants, eggs, fruits, cereals, yoghurt and more. There is also a shared kitchen for those who want to whip up their own meals.

Tropical Paradise | Best Airbnb in Wicker Park

Tropical Paradise Airbnb in Wicker Park

This stunning Airbnb takes interior design talent to the next level. This massive four-bedroom listing has space to sleep up to 14 people, making this a great choice for large groups.

You’ll find plenty of kitchen items to help you get your chef on, and even a fully functioning hot tub. A sunny outdoor patio space is perfect for sipping margaritas or getting some online work done. What’s more? This massive unit is close to public transit, along with an assortment of restaurants and other attractions.

Things to See and Do in Wicker Park

  1. Visit the Flat Iron Arts Building, an all-artist studio building.
  2. Check out the city’s unique culinary scene on a foodie bike tour.
  3. Listen to legendary artists and great live music at Subterranean.
  4. Caffeinate your day at The Wormhole Coffee.
  5. Stroll or picnic at the actual Wicker Park.
  6. Sample legendary Mexican cuisine at Big Star.
  7. Head up to Bloomingdale Trail – also known as the 606 – and enjoy amazing views of the city.

5. Lincoln Park – Best Place to Stay in Chicago for Families

Lincoln Park has got to be the safest place to stay in Chicago. Filled with greenery and plenty of residential neighborhoods, it’s one of the best areas to stay in Chicago to enjoy a true slice of local life.

Sunset at Lincoln Park, Chicago

Home to fantastic attractions including the incredible Lincoln Park, this northern neighborhood was seemingly made for families. It has 1,200 acres of natural space to explore and it boasts a relaxed and tranquil atmosphere.

Here you can marvel at the beautiful architecture, take a stroll along the water and through lush parks, and indulge in many decadent cupcakes.

Hotel Versey Days Inn Chicago | Best Hotel in Lincoln Park

Chicago Cubs-themed rooms in Hotel Versey Days Inn Chicago

This great hotel is located at the heart of Lincoln Park. It’s close to Wrigley Field, and many of Chicago’s top tourist attractions. Modern and spacious, this hotel has large rooms, a fitness centre, and fast Wi-Fi.

The vibe of the place is super chill, the local shops and restaurants are within walking distance, and the staff are helpful and kind. It’s also really convenient for public transport to explore other neighborhoods.

Chicago Getaway Hostel | Best Hostel in Lincoln Park

Five red and black bunkbeds in Chicago Getaway Hostel

This extra-large hostel boasts bright and spacious rooms, with modern amenities and colourful interior design. Chicago Getaway is close to Lake Michigan and just a short subway ride away from Downtown. A FREE breakfast is offered, setting you up for a great day out on the town.

Great Value Artsy Studio | Best Airbnb in Lincoln Park

Great Value Artsy Studio apartment with large painting on wall

This Lincoln Park apartment might just be one of the best value places to stay in all of Chicago. The large studio features an incredibly comfy bed, a perfect mini kitchen that includes a full-sized oven/stovetop, and a Smart TV.

The location is peaceful and walkable to many excellent bars and restaurants. You’ll also be able to access public transit, meaning you can save on expensive Ubers. For the price, you can’t beat this cosy, comfy, and budget-friendly Chicago Airbnb.

Things to See and Do in Lincoln Park

  1. Wander throughout the expansive and stunning Lincoln Park.
  2. Dive deep into the city’s rich and storied history by visiting the Chicago History Museum.
  3. Explore the botanical gardens near the shores of Lake Michigan at the Lincoln Park Conservatory.
  4. Rest and relax on North Avenue Beach, one of Chicago’s most popular beaches.
  5. If you’ve got little ones, head down to the Chicago Children’s Museum.
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FAQs About Finding a Place to Stay in Chicago

Here’s what people usually ask about the areas of Chicago and where to stay.

What To Pack For Chicago

Pants, socks, underwear, soap?! Take it from me, packing for a hostel stay is not always quite as straightforward as it seems. Working out what to bring and what to leave at home is an art I have perfected over many years.

Don’t Let Snorers Keep You Awake!
Don’t Let Snorers Keep You Awake!

Ear Plugs

Snoring dorm-mates can ruin your nights rest and seriously damage the hostel experience. This is why I always travel with a pack of decent ear plugs.

Keep your laundry organized and stink free
Keep your laundry organized and stink free

Hanging Laundry Bag

Trust us, this is an absolute game changer. Super compact, a hanging mesh laundry bag stops your dirty clothes from stinking, you don’t know how much you need one of these… so just get it, thank us later.

Stay Dry With a Micro Towel
Stay Dry With a Micro Towel

Sea To Summit Micro Towel

Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight, and can be used as a blanket or yoga mat if need be.

Make Some New Buddies…
Make Some New Buddies…

Monopoly Deal

Forget about Poker! Monopoly Deal is the single best travel card game that we have ever played. Works with 2-5 players and guarantees happy days.

Reduce Plastic – Bring a Water Bottle!
Reduce Plastic – Bring a Water Bottle!

Grayl Geopress Water Bottle

Always travel with a water bottle! They save you money and reduce your plastic footprint on our planet. The Grayl Geopress acts as a purifier AND temperature regulator. Boom!

Check out my definitive Hotel Packing list for even more top packing tips!

Don’t Forget Travel Insurance for Chicago

Having good travel insurance for when things don’t turn out as planned is a lifesaver. Better safe than sorry.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing.

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

Final Thoughts on Where to Stay in Chicago

Chicago is one of the best places to visit in the USA. It has everything from incredible architecture and extravagant shopping to live music, electric clubs, and amazing restaurants.

By this point, you’ll ideally have a better idea of where to stay. But if these neighborhoods don’t meet your needs, don’t stress: these are just a handful of all that exists in Chicago!

You can also check out the luxurious Gold Coast area for full-on luxury or Oak Park for a suburban feel. Further south, you’ll find the Hyde Park neighborhood bursting with museums and even more green space.

If you’re feeling unsure, my recommendation is to lock in my top pick for the best hotel in Chicago: The Langham. It’s a taste of luxury for your stay in the city, you’ll be treated like absolute royalty. It’s also in an ideal location to make the most of your time in the city with iconic landmarks close by.

If you’re on more of a budget (like I was!), I’d suggest Freehand Chicago. It’s got everything you need for a comfy stay, has great communal areas and is right in the middle of town.

But regardless of where you choose to stay, you can rest assured that you’re in for quite the excursion. From its deep-dish pizza to lake-shore beaches, Chicago is so special and delicious, that I’m sure your first trip won’t be your last!

Lake beach with Chicago skyline behind
Nothing quite beats that lake + city combo.

Last Updated May 2022 by Samantha Shea from Intentional Detours


  1. Atlas, W. (2019, January 4). The Largest Cities In The Midwest.
  2. District, C. P. (2023). Lincoln (Abraham) Park | Chicago Park District. Chicago Park District.
  3. Mission & Values | Navy Pier. Navy Pier. (2023).
  4. Conservatory, L. P. (2022, October 26). Lincoln Park Conservatory & Gardens. Lincoln Park Conservancy – Restoring Lincoln Park’s Art, Architecture and Nature Since 1984.
  5. Choose Chicago. (2023, May 18). North Avenue Beach.