Wondering Where to Stay in Chicago? (MUST READ • 2019)

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Find out where to stay in Chicago, the best places and things to do in Chicago, & the best accomodation in each area!

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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, Chicago is amazing!

But Chicago is a massive city and deciding which area to book in can be incredibly overwhelming. That’s why we wrote this insider’s guide for where to stay in Chicago.

This article is written for travellers, by travellers. It takes a detailed look at the best places to stay in Chicago and organizes them based on your travel interests.

Whether you’re looking to see the top sights, dance the night away, dine on some deep dish pizza, or do a little bit of everything, 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!

 

Quick Tips – Where to Stay in Chicago

 

In a hurry? Here’s my top neighborhood for first-timers:

The Loop
Downtown/The Loop is undoubtedly the most famous and the best area to stay in Chicago. Home to the city’s business district, this area of Chicago is packed with skyscrapers, lively theatres, and picturesque architectural landmarks.
Places to Visit:
  • Take a picture at Cloud Gate, the iconic Bean sculpture
  • Tease your taste buds with a giant sandwich at Eleven City Diner
  • Enjoy great cocktails and delicious food at BIG Bar

 

Where to Stay in Chicago

Looking for a specific place to stay? These are our highest recommendations for the best places to stay in Chicago.

 

Best Hostel in Chicago: Freehand Chicago

Set in stunning Streeterville is Freehand Chicago – our pick for the best hostel in Chicago. This charming hostel is built in a classic 1920’s building and comes complete with stylish décor. It has a cocktail bar, a fitness centre, and on-site laundry facilities. They even provide linens, blankets and plush towels to guests.

View on HostelWorld

 

Best Hotel in Chicago: Fieldhouse Jones

Cool and comfortable, stylish and rustic; these are just a few of the reasons Fieldhouse Jones is our favourite hotel in Chicago. Not only is this hotel close to transit lines, but there are plenty of bars, clubs and pubs nearby. It has comfortable rooms, clean facilities and a friendly staff.

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Best Airbnb in Chicago:

With this basic, convenient and well-priced studio apartment, you have access to a comfortable, queen size bed, full kitchen, on-site laundry facility, free wifi, and an awesome host who will recommend you places to visit, attractions to see in Chicago.

View on Airbnb

 

Chicago Neighborhood Guide

Quick Summary: The Best Places to Stay in Chicago

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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.
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Streeterville

  • 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.
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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.
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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.
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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.
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Chicago is a vast and expansive city.

It is the largest city in the Midwest and is a central hub for arts and entertainment, music, food and culture.

Located on the shores of massive Lake Michigan, Chicago is home to a city population of nearly 3 million, with almost 10 million people living in the metropolitan area. To put this in perspective, New York City and Los Angeles are the only American cities bigger than Chicago.

Chicago is made up of more than 200 neighbourhoods. Spread across 77 community areas and six districts, each neighbourhood has its own unique activities, attractions, populations and history.

This guide will break down Chicago’s best neighbourhood by interest.

Beginning, of course, with Chicago’s most famous neighbourhood Downtown/The Loop. Located at the centre of the city, this part of Chicago is bursting with history and culture, landmarks, restaurants and bars.

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

Meanwhile, Wicker Park, west of Downtown, is the city’s coolest neighbourhood 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 greenest neighbourhoods in the city with more than 1,200 acres of green space. There is also a zoo, many museums, and plenty of kid-friendly activities.

If you’re still not sure where to stay in Chicago, fear not. Because we’re about to explore each of these neighbourhoods in detail below.

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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 neighbourhoods in Chicago.

 

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

Downtown/The Loop is undoubtedly the most famous neighbourhood in Chicago. Home to the city’s business district, this area of Chicago is packed with skyscrapers, lively theatres, and picturesque architectural landmarks. It’s also dotted with incredible restaurants where you can sample some of Chicago’s most delicious and iconic foods. That’s why it’s our pick for where to stay if you’re visiting for the first time.

Designed in a grid pattern, navigating Downtown Chicago couldn’t be easier – even if you aren’t the best with a map. If you like to explore on foot, you’ll love wandering the city streets and steeping yourself in Chicago’s rich history and diverse culture.

Downtown, Chicago

 

Best Hostel in Downtown/The Loop: HI Chicago

At HI Chicago, guests have all of the city’s top tourist attractions, art galleries, museums, shops and restaurants right at their doorstep. This hostel comes complete with more than 500 comfortable beds. They offer free daily breakfast, free bed linens and free walking tours throughout Chicago.

View on HostelWorld

 

Best Hotel in Downtown/The Loop: Central Loop Hotel

The Central Loop Hotel has stylish décor, 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. All of this combined makes it our choice for where to stay in Chicago in the Downtown area.

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Best Hotel in Downtown/The Loop: Best Western Grant Park Hotel

Set at the centre of Downtown Chicago, the Best Western Grant Park is ideally located for exploring the city. Just a few minutes walk from top attractions, including Willis Tower and the famous Bean sculpture. It comes complete with a coffee bar, swimming pool, fitness centre and a comfortable lounge bar.

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Best Airbnb in Downtown/The Loop: Modern loft for 2

With this basic, convenient and well-priced studio apartment, you have access to a comfortable, queen size bed, full kitchen, on-site laundry facility, free wifi, and an awesome host who will recommend you places to visit, attractions to see in Chicago.

View on Airbnb

 

Things to See and Do in Downtown/The Loop

The loop ttd Chicago

– Take a picture at Cloud Gate, the iconic Bean sculpture.

– Stand at the centre of Millennium Park.

– Tease your taste buds with a giant sandwich at Eleven City Diner.

– See incredible works of art at the Art Institute of Chicago.

– Climb to the 99th floor of Willis Tower and enjoy sweeping views out over the city.

– Challenge a friend to a friendly round of ping-pong at AceBounce.

– Sample curious cocktail at ROOF on theWit.

– Enjoy great cocktails and delicious food at BIG Bar.

– Kickstart your day with an amazing breakfast at Wildberry Pancakes and Café.

– Dig into an exquisite Italian dinner at Trattoria No. 10.

 

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 neighbourhood of Streeterville – also on of the best places to stay in Chicago if money is tight.

One of Streeterville’s most famous and fun attractions is Navy Pier. A bright and vibrant hub for excitement and entertainment, 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 Amazing Chicago’s Funhouse Maze, there’s something for everyone at Navy Pier.

Not only is Streeterville our pick for fun and games, but it’s our pick for where to stay in Chicago on a budget thanks to its great hostel options. Note that you can save even more money if you avoid visiting Chicago at the weekend.

Streeterville, Chicago

 

Best Hostel in Streeterville: Freehand Chicago

Set in stunning Streeterville is Freehand Chicago – our top pick for where to stay in Streeterville. This charming hostel is built in a classic 1920’s building and comes complete with stylish décor. It has a cocktail bar, a fitness centre, and laundry facilities on-site. They even provide linens, blankets and plush towels to guests.

View on HostelWorld

 

Best Hotel in Streeterville: Raffaello Hotel Chicago

The Raffaello Hotel is modern, stylish and impossibly chic. Conveniently located in Streeterville, this four-star hotel is a short walk from the Magnificent Mile, Michigan Avenue and Chicago’s most famous landmarks. There are plenty of restaurants, bars and clubs nearby, so you won’t need to walk far to find a good time.

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Best Hotel in Streeterville: Dewitt Hotel and Suites

Located in trendy Streeterville, this charming three-star hotel is within walking distance of great restaurants, chic shopping, trendy bars, and top tourist sights. It has amazing wellness amenities, like a gym and a sauna. You won’t believe your eyes when you see the view from the rooftop terrace.

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Best Airbnb in Streeterville: 1 of 4 bunk beds in a shared bedroom

Somewhere between a hostel and hotel, you’ll find the amenities you need! This listing is for one twin bunk in a room with four total bunks, so you will have up to 3 roommates. The room has a private bathroom and lockers for storing valuables. Each bunk features a curtain for privacy, reading lamp, and power outlet. Linens and towels are included, as is regular housekeeping service.

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Things to See and Do in Streeterville

Streeterville ttd Chicago

– Ride thrilling ride at Navy Pier.

– Rent bikes and ride the Lakefront Trail.

– Explore exhibits honouring local sports legends at the Chicago Sports Museum.

– Listen to incredible jazz at the Winter’s Jazz Club.

– Play arcade games and enjoy a few drinks at FTW Chicago.

– Down a pint and enjoy a great night out at the Beer Garden at Navy Pier.

– Sip cocktails on the romantic rooftop at Drumbar Chicago.

– Dig into a piece of savoury pizza at Blaze Pizza.

– Eat delicious burgers, fries and American fare at Epic Burger.

– Enjoy a flavourful bowl of soup at Ramen Misoya.

 

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 epicentre for nightlife making it one of the best areas to stay in Chicago for those who want to party.

Sprinkled throughout this lively neighbourhood are 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 an amazing array of restaurants. Offering up everything from traditional American fare to fashionable fusions, your taste buds will be amazed by all the culinary adventures available in River North.

River North, Chicago

source: hifivephotography.com

 

Best Hostel in River North: Found Hotel Chicago River North

Located in lively River North, Found Chicago offers all the luxury and convenience of a hotel at an affordable price. This stylish and charming property is just steps from some of the best bistros, bars and shops in the city. It has comfortable rooms, free wifi, and an on-site bar, café and restaurant.

View on HostelWorld

 

Best Hotel in River North: Fieldhouse Jones

Cool and comfortable, stylish and rustic; these are just a few of the reasons Fieldhouse Jones is our favourite hotel in River North. Not only is this hotel close to transit lines, but there are plenty of bars, clubs and pubs nearby. It has comfortable rooms, clean facilities and a friendly staff.

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Best Hotel in River North: Hotel Felix

The Hotel Felix is a stylish and modern property in Chicago’s vibrant River North neighbourhood. It has large rooms, a range of facilities, and great attractions, like the Magnificent Mile, are just a few minutes away on foot. There is also a myriad of restaurants, and cafes, and Chicago’s best bars nearby.

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Best Airbnb in River North: Cozy one bedroom with impressive views of Chicagos skyscrapers

This luxury studio comes complete with a spacious living and sleeping area, bathroom, full kitchen, and balcony. The building is fully loaded with amenities, ranging from the pool deck to basketball court to the steam room and sauna.

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Things to See and Do in River North

North River ttd Chicago

– Aim for a lucky strike at 10pin Bowling Lounge.

– Enjoy lowkey and delicious American dishes at Baptiste & Bottle.

– Dig into a succulent plate of Italian food at Bar Lupo.

– Spend the night enjoying live music and unique cocktails at The Bassment.

– Visit the iconic House of Blues.

– Laugh to established and up-and-coming comedians at The Comedy Bar.

– Party the night away at Sound-Bar.

– Dance until the early hours at Disco Chicago.

– Rub shoulders with Chicago royalty at Studio Paris.

– Listen and dance to all the hottest tracks at two-tiered PRYSM Nightclub.

 

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4. Wicker Park – Coolest Neighbourhood in Chicago

One of the coolest and best neighbourhood to stay 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.

Music fans will adore staying in Wicker Park. This dynamic district is where you’ll find some of the city’s most famous live music venues, including the Double Door and 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.

Wicker Park, Chicago

source: trulia.com

 

Best Hostel in Wicker Park: Holiday Jones

Located in trendy Wicker Park, Holiday Jones gives guests the opportunity to experience Chicago like a local. There are plenty of bars, restaurants and shops nearby, and Downtown is just a short train ride away. Beds come with fresh linens and towels, and luggage storage. There’s also a fantastic restaurant on-site.

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Best Hotel in Wicker Park: Ruby Room Spa & Wellness Hotel Chicago

Ruby Rooms is a relaxing and luxurious spa hotel set in the centre of Wicker Park. It comes complete with a garden, library and wellness centre, perfect for a day of pampering. Here you’ll find a great variety of bistros, bars and boutiques at your doorstep.

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Best Hotel in Wicker Park: Urban Holiday Lofts

Our best recommendation for where to stay in Wicker Park, Urban Holiday Lofts are stylish and rustic. Ideally located in this trendy district, these lofts are close to well-known attractions, hip bars and chic cafes. This modern three-star property has a relaxing on-site bar, spacious rooms, and a free shuttle service.

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Best Airbnb in Wicker Park: Charming two-bedroom and one bathroom loft in Wicker Park

Each bedroom has high ceilings, luxury fixtures, and a comfy Queen bed to guarantee a good night’s sleep. The building is conveniently located just three blocks from the coveted Six Corners intersection at Damen, Milwaukee, and North Avenues.

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Things to See and Do in Wicker Park

Wicker Park ttd Chicago

– Visit the Flat Iron Arts Building, an all artist studio building.

– Browse the stacks for your new favourite book at Quimby’s Bookstore, an independent shop.

– Listen to legendary artists and great live music at Subterranean.

– Line up and get ready for the most amazing tacos at Big Star.

– Try incredible diner-style dishes at Dove’s Luncheonette.

– Start your day with a satisfying and indulgent breakfast at Mindy’s HotChocolate.

– Sink your teeth into a tasty burger at Presidio.

– Head up to Bloomingdale Trail – also known as the 606 – and enjoy amazing views of the city.

– Sip extraordinary cocktails on the rooftop at Whiskey Business & Fry Bar.

 

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

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 areas to stay in Chicago and is where you can enjoy a true slice of the local life.

Home to fantastic attractions including the Lincoln Park Zoo and the eponymous park, this northern neighbourhood is our pick for where to stay in Chicago for families. It’s one of the greenest districts with more than 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.

Lincoln Park, Chicago

 

Best Hostel in Lincoln Park: Chicago Getaway Hostel

This extra-large hostel boasts bright and spacious rooms, with modern amenities and sophisticated décor. Located in Lincoln Park, this hostel is close to the lake and is just a short subway ride away from downtown. Complimentary breakfast is included, setting you up for a great day on the town.

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Best Hotel in Lincoln Park: Inn at Lincoln Park

This charming two-star hotel is well situated in Lincoln Park. North of downtown Chicago, this hotel is a short walk from restaurants, cafes, attractions and tourist landmarks. It has a range of facilities, including a fitness centre and dry cleaning service. Its large rooms are perfect for families.

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Best Hotel in Lincoln Park: Hotel Versey Days Inn Chicago

This great hotel is located at the heart of Lincoln Park. It’s is close to the Lincoln Park Zoo, Wrigley Field and many of Chicago’s top tourist attractions. Modern and spacious, this hotel has large rooms, a fitness centre and free internet throughout. This is our pick for where to stay in Lincoln Park.

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Best Airbnb in Lincoln Park: Studio apartment with one bedroom

Studio apartment located in the desirable area right between Lincoln Park/DePaul and Lake View. The unit has one bedroom, complimentary WiFI, a smart TV with Netflix and an onsite laundry facility and bike room.

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Things to See and Do in Lincoln Park

Lincoln Park ttd Portland

– See all your favourite animals – from lions, tigers and bears to birds, reptiles and fish – at the Lincoln Park Zoo.

– Wander throughout the expansive and stunning Lincoln Park.

– Explore the botanical gardens near the shores of Lake Michigan at the Lincoln Park Conservatory.

– Dive deep into the city’s rich and storied history at the Chicago History Museum.

– Rest and relax on North Avenue Beach.

– Tease your taste buds by digging into to a stack of pancakes at Batter & Berries.

– Eat an incredible pot roast at Nookies.

– Try Chicago’s best pizza pot pies at Chicago Pizza & Oven Grinder.

– Sample unique flavours and sweet treats at Molly’s Cupcakes.

 

Obtaining a Tourist Visa to Visit Chicago

 

If you are visiting Chicago from outside the US, then you will need a Visa to enter the country. The easiest way to obtain this is by applying for an ESTA Visa in advance, online. Requirements for an ESTA do vary depending on your nationality so do check conditions before applying.

 

Final Thoughts

Chicago is a thrilling city. It has everything from incredible architecture and extravagant shopping to live music, electric clubs and amazing restaurants. No doubt, Chicago is a city that is certainly worth your time and hard-earned travel dollars!

In this guide, we looked at the top five neighbourhoods in Chicago. To give you a quick recap, our choice for the best neighbourhood is River North. Our recommendation for the best hotel is Fieldhouse Jones because of it’s stylish décor, comfortable setting and it’s unbeatable location in River North.

Our pick for the best hostel is Freehand Chicago thanks to its incredible Streeterville location, its charming 1920s aesthetic, and its incredible amenities.

Have we missed anything? Are you still wondering where to stay in Chicago? Let us know in the comments below!

Don’t forget to sort your travel insurance! We’ve put together a roundup of the best travel insurance for backpackers – check it out here, or if you’re low on time, get a quote from World Nomads now, our favourite travel insurance provider.

 

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