Cheap Hotels in Chicago – The Most Budget-Friendly Stays In The Windy City

Welcome to the Windy City, where the skyscrapers are tall, the pizzas are deep, and the hotel prices? Well, they can blow your budget faster than a gust off Lake Michigan if you’re not careful.

But before you resign yourself to a night under the neon glow of The Bean, let me guide you through the urban jungle to find those hidden gems where the only thing lighter than your wallet is your heart as you explore this vibrant city.

This is about finding a place to crash that won’t crash your financial plans, a sweet spot where cost efficiency meets comfort without compromising on the Chicago experience.

Navigating the choppy waters of affordable accommodation in a city famed for its architectural marvels and culinary feats can be daunting. Yet, here we stand (or sit comfortably, I don’t judge) at the threshold of discovery.

From the eclectic neighborhoods echoing with the blues to the bustling streets of the Loop, I’ve scouted out 12 wallet-friendly hotels and hostels that prove you can enjoy the Chi-Town charm on a dime. So, grab your notepad, or whatever digital equivalent you fancy, and let’s dive into the urban oasis of affordability.

1. The Freehand Chicago

Nestled in the heart of River North, a district as famous for its art galleries as it is for its nightclubs, The Freehand Chicago blurs the lines between hostel and hotel with an artistry all its own. This isn’t just a place to sleep; it’s a place to live, albeit temporarily. The vibe here is a cocktail of bohemian and chic, shaken with a dash of communal spirit, and served in a vintage glass. It’s the kind of spot where you can mingle with fellow travelers over a cup of coffee in the café by morning, and by night, debate the merits of Picasso versus Pollock over a bespoke cocktail at the Broken Shaker, the in-house bar that’s earned its stripes (and then some) in the local scene.

Highlights: Beyond the social atmosphere, what sets The Freehand apart is its range of accommodations. From the shared quarters, where stories and Instagram handles are exchanged, to the private rooms that whisper sweet nothings of solitude and comfort, there’s a space for every traveler and budget. And let’s not overlook the shared kitchen, a boon for those looking to pinch pennies by cooking their own meals.

Practical Tip: For those eyeing the best deals, timing is everything. Visit during the colder months, when Chicago’s chill keeps the fair-weather tourists at bay but ignites the city’s cultural scene, offering a more intimate (and affordable) experience.

Book Your Stay – Here

The Freehand Chicago - Cheap Hotels in Chicago: Where to Stay for Less Than $100 a Night
The Freehand Hotel

2. Chicago Getaway Hostel

If the walls of Chicago Getaway Hostel could talk, they’d tell tales of budding friendships, impromptu guitar jams, and the kind of spontaneous adventures that become the stuff of legend. Situated in the leafy streets of Lincoln Park, a stone’s throw from the eponymous park and zoo (which, by the way, is free), this hostel serves as a beacon for budget travelers with a thirst for exploration and connection.

The building itself is a blend of historical charm and modern flair, where the warmth of exposed brick meets the cool of contemporary design. Here, community is the name of the game, with ample common spaces designed to foster interaction among guests from all corners of the globe.

Highlights: What sets the Getaway apart, aside from its prime location and welcoming vibe, is the little extras that add up to a big difference. The complimentary breakfast is a hearty way to start your day, and the hostel’s calendar is always brimming with events, from pub crawls to pizza tours, ensuring your Chicago itinerary is as full as your heart (and stomach).

Practical Tip: Embrace the spirit of the city on two wheels. The hostel’s proximity to bike rentals and scenic paths offers a unique way to take in the sights, from the shores of Lake Michigan to the historic architecture dotting Lincoln Park.

Book Your Stay – Here

Chicago Getaway Hostel - Cheap Hotels in Chicago: Where to Stay for Less Than $100 a Night
Chicago Getaway Hostel

3. HI Chicago Hostel

Imagine a place where the pulse of the city meets the warmth of a global community. HI Chicago Hostel stands proudly in the heart of the Loop, inviting travelers to dive into the city’s bustling core while offering a respite that feels a world away. It’s more than a place to sleep; it’s a hub of cultural exchange, eco-friendly practices, and endless possibilities.

With a facade that whispers of Chicago’s grand architectural heritage and interiors that speak the language of modern, sustainable travel, HI Chicago blends the best of many worlds. Offering a mix of dormitory-style rooms for those keen to make new friends, and private rooms for those craving a quiet retreat after a day of urban adventures, this hostel ensures comfort and connection don’t have to be mutually exclusive.

Highlights: What truly sets HI Chicago apart are its green initiatives and dedication to community outreach. From recycling programs to local volunteer opportunities, guests are invited to not just travel, but travel with purpose. And with amenities like free Wi-Fi, a fully equipped guest kitchen, and spacious common areas, the hostel stands as a testament to the fact that affordable travel can be luxurious in its own right.

Practical Tip: Membership has its perks. Joining Hostelling International not only supports their mission of fostering understanding through travel but also nets you a discount on your stay. Plus, with the hostel’s central location, you’re just steps away from iconic sights like Millennium Park, the Art Institute of Chicago, and the vibrant Theater District, making it an ideal base for cultural exploration.

Book Your Stay – Here

HI Chicago Hostel - Cheap Hotels in Chicago: Where to Stay for Less Than $100 a Night
HI Chicago Hostel

4. Motel 6 Chicago O’Hare – Schiller Park

Not all treasures lie within the city’s heart. Sometimes, a short jaunt to the outskirts uncovers spots like Motel 6 Chicago O’Hare – Schiller Park, where simplicity and savings go hand in hand. Ideal for the traveler catching an early flight or seeking a straightforward stay near the airport, this Motel 6 offers the no-frills comfort that the brand is known for, with the added bonus of Chicago’s attractions within reach.

Located conveniently close to O’Hare International Airport, this motel strips down the travel experience to its essentials, focusing on clean, comfortable rooms and the kind of service that makes transit a breeze. With a commitment to affordability and accessibility, it serves as a practical base for both the business traveler and the budget wanderer alike.

Highlights: The free airport shuttle service is a godsend for those with hefty luggage or tight schedules, eliminating one of travel’s common stresses. Additionally, the availability of free parking makes this motel a smart choice for road trippers exploring the Great Lakes region.

Practical Tip: While staying on the outskirts might seem disconnected, public transport options like the Metra and CTA Blue Line are nearby, offering direct access to downtown Chicago. It’s a way to enjoy the city’s buzz by day and retreat to peacefulness by night, all while keeping your budget firmly grounded.

Book Your Stay – Here

Motel 6 Chicago O'Hare - Schiller Park
Motel 6 Chicago O’Hare – Schiller Park

5. Red Roof Inn

With multiple locations scattered around Chicago, Red Roof Inn stands as a beacon for travelers seeking the holy grail of affordability, comfort, and convenience. Known for their straightforward approach to lodging, Red Roof Inn ensures that the essentials are done right: comfortable beds, clean rooms, and service with a smile.

Whether you’re in town for a business meeting or a deep-dive into the city’s legendary blues scene, Red Roof Inn offers a hassle-free basecamp. Their pet-friendly policy means your furry friends can join in on the adventure, making it a perfect pick for pet owners on the move.

Highlights: Aside from the basics, what sets Red Roof Inn apart is its commitment to keeping you connected. Free Wi-Fi in every room ensures that planning your next day’s itinerary or catching up on emails is as easy as pie. And with several locations, you’re never too far from the action, whether it’s a game at Wrigley Field or a stroll along the Magnificent Mile.

Practical Tip: Leverage the RediRewards program to its fullest. Not only can you earn points towards future stays, but members often get access to exclusive deals and discounts, making an already affordable stay even sweeter.

Red Roof Inn - Cheap Hotels in Chicago: Where to Stay for Less Than $100 a Night
Red Roof Inn

6. The Pittsfield Hotel – Apartments + Suites

For those who dream of living like a local without forking over a month’s rent, The Pittsfield Hotel – Apartments + Suites offers a unique alternative to the traditional hotel stay. Nestled in the heart of the city, this historic building has been transformed into a collection of apartment-style accommodations, blending the comfort of home with the excitement of city life.

The Pittsfield Hotel’s charm lies in its ability to offer guests their own slice of Chicago. With fully equipped kitchens, spacious living areas, and the privacy of separate bedrooms, these apartments are ideal for families, groups of friends, or solo travelers looking for a bit more elbow room.

Highlights: Its location is unbeatable. Steps away from Millennium Park, guests find themselves in the shadow of the Cloud Gate (affectionately known as The Bean), with the Art Institute of Chicago, State Street shopping, and endless dining options all within walking distance. It’s your personal Chicago, ready to explore at your own pace.

Practical Tip: Embrace the opportunity to cook your own meals in the fully equipped kitchen — a surefire way to save on dining out. Local grocery stores are just a stone’s throw away, and with Chicago’s famed farmers markets in full swing during the summer months, you can whip up a meal that’s both fresh and frugal.

The Pittsfield Hotel – Apartments + Suites
The Pittsfield Hotel – Apartments + Suites

7. Chicago Parthenon Hostel

Nestled in the vibrant West Loop neighborhood, Chicago Parthenon Hostel offers a cozy, friendly base for travelers eager to explore Chicago’s culinary and cultural riches. It’s a place where the welcome is warm, the beds are comfy, and the adventures are just outside the door.

This hostel stands as a testament to Chicago’s ability to blend the old with the new. The building, with its classic architecture, houses modern amenities and comfortable accommodations, from private rooms to dormitory-style setups perfect for making new friends.

Highlights: The on-site restaurant, serving up hearty, home-cooked meals at a fraction of the city’s usual prices, is a major draw. But perhaps the greatest highlight is the hostel’s location. Situated within walking distance of some of the best eateries in the city, as well as the United Center, guests are perfectly positioned to dive into the local scene.

Practical Tip: Don’t miss exploring Greektown, just a few blocks away, where authentic Greek cuisine and culture fill the air. It’s an experience that will enrich your stay without emptying your pockets. Additionally, the hostel’s knowledgeable staff are more than happy to recommend hidden gems and must-visit spots, ensuring you get the most out of your Chicago adventure.

Book Your Stay – Here

Chicago Parthenon Hostel - Cheap Hotels in Chicago: Where to Stay for Less Than $100 a Night
Chicago Parthenon Hostel

8. Heart O’ Chicago Motel

For those who appreciate a good throwback, the Heart O’ Chicago Motel offers a nostalgic retreat with its vintage charm and mid-century design. This family-run establishment reminds us that sometimes, the simplest things can bring the greatest pleasure.

Situated in the Edgewater neighborhood, this motel harks back to a time when road trips ruled and motels were the go-to for weary travelers looking for a night’s rest. Today, it provides a clean, comfortable, and remarkably affordable stay, with easy access to some of Chicago’s best attractions.

Highlights: Guests will appreciate the free parking – a rare find in a city like Chicago – and the proximity to public transportation, making it easy to explore the city. The friendly, personal service is another highlight, with staff going out of their way to ensure your stay is memorable.

Practical Tip: Take advantage of the motel’s location to explore the nearby beaches of Lake Michigan, the historic Bryn Mawr district, and Andersonville’s bustling Clark Street, known for its unique shops, restaurants, and nightlife. The Heart O’ Chicago offers a quiet, comfortable base to return to after a day (or night) full of exploration.

Book Your Stay – Here

Heart O' Chicago Motel
Heart O’ Chicago Motel

9. The Hollander

The Hollander stands proudly in the vibrant and artsy neighborhood of Wicker Park, inviting travelers to experience a unique social-stay concept that’s as innovative as it is inviting. Housed in a restored historic building, this hostel-hotel hybrid is perfect for the social traveler looking to connect with others without sacrificing style or comfort.

The Hollander’s design-forward approach blends industrial chic with modern comforts, offering guests a range of accommodations from private rooms to shared social dorms. What sets this establishment apart is its embrace of social media connectivity, allowing guests to connect via Instagram before even checking in, fostering a sense of community and camaraderie.

Highlights: Aside from its stylish accommodations, The Hollander is also home to a bustling café and bike rental service, encouraging guests to explore the local area on two wheels. Its location in Wicker Park means you’re just steps away from some of Chicago’s best coffee shops, bars, and record stores, making it a haven for those looking to dive deep into the city’s hipster heartland.

Practical Tip: Make the most of The Hollander’s social spaces to meet fellow travelers and locals alike. The communal areas are designed to encourage interaction, making it an ideal spot for solo travelers looking to make new friends. Additionally, the bike rental service offered by the hostel is not only a nod to sustainable travel but also the perfect way to see the city from a new perspective, navigating through neighborhoods with ease and soaking in the urban vibe.

The Hollander
The Hollander

10. The Flats at Loyola Station

The Flats at Loyola Station offers a unique and personalized lodging experience in Chicago’s lively Rogers Park neighborhood. Situated just steps from the scenic Loyola University campus and the shores of Lake Michigan, this boutique hotel presents an attractive option for travelers seeking comfort, convenience, and a touch of local flavor.

The Flats at Loyola Station features fully furnished apartments, providing guests with a home-away-from-home experience. Each flat is equipped with modern amenities, including full kitchens, spacious living areas, and private bathrooms, making it ideal for both short-term and extended stays.

Highlights: The standout feature of The Flats is undoubtedly its location. Rogers Park is one of Chicago’s most diverse and vibrant neighborhoods, known for its eclectic dining scene, colorful murals, and community-oriented vibe. The hotel’s proximity to the Red Line also means that guests have easy access to downtown Chicago and its myriad attractions.

Practical Tip: Embrace the local community by exploring the neighborhood’s many cafes, shops, and public parks. The hotel staff are great resources for recommendations on the best local spots. Additionally, taking a stroll along the Loyola campus or heading to nearby Loyola Beach offers a pleasant respite from the city’s hustle and bustle, providing a glimpse into Chicago’s more laid-back side.

Book Your Stay – Here

The Flats at Loyola Station
The Flats at Loyola Station

11. FieldHouse Jones

FieldHouse Jones takes the concept of a budget stay and turns it on its head, offering an eclectic and engaging experience that reflects the adventurous spirit of Chicago itself. Located in the dynamic Near North Side neighborhood, this boutique hotel is a tribute to the city’s rich sports history and vibrant community life, offering a unique blend of art, culture, and hospitality.

With its blend of private and shared accommodations, FieldHouse Jones caters to a wide array of travelers, from solo explorers to families and groups. The interior is a feast for the eyes, featuring a collection of vintage sports memorabilia and local art that tells the story of Chicago’s storied past and present.

Highlights: The hotel boasts a variety of communal spaces, including a café, a vintage game room, and even a craft workshop space, encouraging guests to engage with one another and the city in new and meaningful ways. The on-site café serves up delicious local fare, making it easy to grab a bite before heading out to explore.

Practical Tip: Don’t miss the chance to attend one of the hotel’s hosted events, which range from art shows to local history talks. It’s a fantastic opportunity to dive deeper into the fabric of Chicago while connecting with fellow travelers and locals alike.

12. Aloft Chicago Mag Mile

For those looking to sprinkle a little luxury into their budget-conscious travels, Aloft Chicago Mag Mile manages to strike the perfect balance. Situated just steps from the Magnificent Mile, this hotel offers sleek, modern accommodations with just the right amount of flair, all within an arm’s reach of Chicago’s most iconic attractions.

Aloft hotels are known for their contemporary design and vibrant social scenes, and the Mag Mile location is no exception. From the spacious, tech-savvy rooms to the lively W XYZ bar, Aloft provides a stylish backdrop to your Chicago adventures without stretching your budget.

Highlights: Amenities like the indoor pool, 24-hour fitness center, and pet-friendly policies ensure that every aspect of your stay is as enjoyable as it is affordable. Plus, the hotel’s proximity to landmarks like Navy Pier, Millennium Park, and the Art Institute of Chicago means you’re never far from the next item on your itinerary.

Practical Tip: Keep an eye out for special promotions and package deals, particularly during the off-peak seasons. Booking directly through the hotel’s website can also unlock discounts and perks, making this chic stay even more accessible.

Book Your Stay – Here

Aloft Chicago Mag Mile
Aloft Chicago Mag Mile

From the eclectic charm of FieldHouse Jones to the chic convenience of Aloft Chicago Mag Mile, our exploration of Chicago’s best budget-friendly accommodations reveals a city that’s not only rich in culture and history but also in opportunities for travelers to immerse themselves without breaking the bank. Each of these 12 spots offers its own unique take on what it means to experience Chicago, ensuring that no matter where you choose to stay, you’re guaranteed a memorable and affordable adventure.

So pack your bags and ready your appetite for exploration, because Chicago awaits. With these budget-friendly stays as your base, the Windy City’s world-class museums, iconic architecture, vibrant neighborhoods, and culinary delights are yours to discover. And remember, the true essence of travel isn’t found in the luxury of your accommodations but in the richness of your experiences. Chicago, with its open arms and endless possibilities, proves just that.