8 Unique Chicago Stays That Aren’t Your Boring Chain Hotels (2024)

Social media influence or an aptitude to try something new – whatever the reason, travelers are seeking alternative accommodations in Chicago and different places to stay rather than a hotel. Why? Despite the luxurious accommodation options and design-forward amenities, many tourists find hotels to be boring, colorless, and lacking personality.

Not to mention, hotels are hella expensive!

So, if you are looking at unique Chicago stays to switch it up a little, plan a staycation, or want to immerse in local culture, there are plenty of non-traditional accommodations to choose from, depending on your mood and budget.

1. Short Term Chicago Vacation Rentals

Looking for cheap Chicago accommodation options, quality food, and a place to stay that feels like home? Short term vacation rentals might be the answer. This type of stay comes in many different sizes and shapes, and with the rise of Airbnb, many individual landlords in Chicago are renting out their properties in the short term.

So why should you choose a short term rental and not a hotel?

• You have your own space (lots of privacy!)
• You can cook your own meals in the kitchen (no reason to eat unhealthy food)
• Invite your friends and family (have a cozy gathering in the living room)
• Choose a place according to your budget.

However, as a tourist in Chicago, make sure that you are fully researching and reading reviews of such rentals across the city to ensure that they are reliable and authentic. Here are some questions that you must ask yourself and the landlord before renting out this type of stay;

• Do you want to stay in a vibrant neighborhood like River North or a quaint one like Lincoln Park?
• Will this short-term rental offer easy access to public transportation?
• What amenities are necessary for your stay (e.g., WIFI, parking, laundry facilities)?
• What are the house rules, security deposits, and cleaning fees?
  

2. Chicago Bed and Breakfast Options

Chicago’s B&Bs are neighborhood businesses consisting of not more than four rooms, typically. And if you are looking for a homely environment with local hospitality, there is no better option than Chicago’s B&Bs. The hosts know the neighborhood and the whole city like the back of their hand, and what better way to know the city than living with its local residents? Don’t know about you, but we love Villa D’ Citta Bed & Breakfast and The Publishing House Bed and Breakfast!

But how does a B&B add that personal touch and magic to your stay?

• Experience a personal interaction with locals (feels like home!)
• Enjoy a warm welcome and a small number of guests in the same house
• Receive insider tips from your local hosts
• Perfect for a leisurely stay or a romantic getaway.

Since a B&B is all about personal touches, you can expect a genuinely warm welcome like fresh towels, coffee, basic toiletries and decorated rooms. These are some questions that you should be asking before staying in one;

• Which B&Bs are highly recommended in the city, and what time can you check in/check out?
• Will you get free Wi-Fi or a broadband line?
• What size are the beds, and will you receive a larger bed on request?
• How will your stay be made comfortable, such as laundry facilities, adaptors for electrical sockets, and an en-suite bathroom?
  

3. Chicago Boutique Accommodations

Chicago boutique hotels have 10 to 100 rooms, but you know what? No two boutique hotels will look alike! They are extremely personalized and more niche than cookie-cutter and luxurious chain hotels. The staff is family-like, which means there will be no compromise on your luxury, comfort, and intimacy. Boutique hotels are some of the best alternatives to hotels in Chicago and are operated by local entrepreneurs. The Wheeler Mansion, The Robey, and SOPHY – Hyde Park are our top picks!

And what makes boutique hotels the hottest alternative accommodation in Chicago?

• Rooms with a character and charm!
• Complimentary breakfasts!
• A guest-first approach and pet-friendly rules
• Unique interior designs (made for your Instagram feeds!)
• Located in trendy spaces, like factories with soaring ceilings, Tuscan-style villas, and historic landmark buildings.

To make sure you’re staying comfortably, keep an eye out for the following aspects of a boutique hotel;

• Do you prefer being social and communal while being in the West Loop or looking for a cozy and quiet spot in Wicker Park?
• Does the boutique hotel offer any “wow factor,” like group activities, upscale amenities, or top-of-the-line entertainment?
• Is it tucked away or in an upscale neighborhood, and does it provide you access to public transportation?
• How open is the boutique hotel management to feedback and special requests?
  

4. Chicago RV Rentals

RV rentals are trending these days and are probably something you won’t forget anytime soon. If you are looking for different places to stay in Chicago and don’t want to choose a boring hotel once again, why not rent an RV? You can enjoy quirky accommodations, traveling, and meals in one package, and they cost less than hotels.

And what is it that makes RV rentals much more cool than hotels? You won’t believe us until you see it yourself, that…

• You can bring twice as many people as you can squeeze into a hotel room
• They are perfect for day trips or staying close to a national park or other remote locations
• You can make your own meals, watch birds, hike, watch the sunrise, and do more anytime and anywhere you like.

But before heading out, make sure you are choosing the right RV for your traveling needs. RV rentals, caravans, and glamping are crowd favorites in Chicago, as we can see from the above points, and they always enjoy phenomenal favoritism from digital nomads, families, and couples. However;

• You should assess the overall charges of the RV, including rent, environmental expenses, etc.
• You should inquire about the fees for the items inside the vehicles, like bedding and cookware.
• Ask all the right questions beforehand, such as how check-in works and where to leave the vehicle when you want to check out.
  

5. Vacation Rentals In Chicago

Vacation rentals feel like a home-away-from-home as they are some of the most unique Chicago stays. Want to stay in luxurious suites of Level Chicago Old Town, a stone’s throw away from the Chicago History Museum or Second City Theatre? Or the air-conditioned Forrestville Ave Large Suite to enjoy a round of well-maintained golf courses during your stay?

Beachfront locations, pet-friendly accommodations, air-conditioned apartments, and ample parking space – there are so many reasons why people love vacation rentals. Want to know a few of them?

• They are expensive, yes, as compared to hotels in Chicago, but more luxurious and comfortable.
• Have flexible check-in and check-out times
• Offer longer stays and larger spaces for your whole family or group
• You can have the entire property to yourself, including living areas, kitchens and bedrooms.

However, before booking, you must consider the following factors;

• Whether the vacation rental is close to major attractions in Chicago (or the ones you want to cover in your itinerary)
• What amenities are offered (parking? WIFI? Kitchen facilities?)
• What are the house rules, pet policies, and other restrictions, such as check-in and check-out times?
• Always read reviews of vacation rentals and compare their prices before booking them.
  

6. Hostels In Chicago

If you want a budget-friendly alternative to hotels in Chicago, hostels are your perfect match. The trendy Chicago Parthenon Hostel, Chicago Getaway Hostel, and HI Chicago family hostel are the trendiest Chicago accommodation options for solo travelers and backpackers, and sometimes couples as well. Along with private and dormitory-style spaces and comfortable features, you will get plenty of time to make new friends while saving lots of bucks while staying at a hostel in Chicago.

Here is why Chicago hostels are so amazing;

• You can save money by booking them during low season (perfect for travelers on a budget!)
• Book at least a month before your stay in Chicago, and you will get the best bargains for the hostel.
• The hostels bring you closer to Chicago’s most popular attractions, like Wrigley Field Stadium, Navy Pier, and Millennium Park.
• Free towels, shared kitchens, and bicycle rental options make them exciting alternative accommodations in Chicago.

Before you book a hostel, go through the following checklist;

• Is it located in a good location, preferably near public transport?
• Does it offer lockers or other features to secure your valuables?
• What are the check-in and check-out times (you wouldn’t want to be locked out!)
• How is the atmosphere at the hostel (is it more likely to host weekly BBQs or swings towards a quiet and relaxed space?)
  

7. Guesthouses In Chicago

Guesthouses have more personality than hotels and are slightly larger establishments than B&B’s. Guesthouses in Chicago are located in some of the finest neighborhoods like Rogers Park, Bronzeville, Ravenswood Lincoln Square, etc. If you are looking for a hotel alternative in Chicago, guesthouses come up as a cost-effective accommodation with exceptional services like gardens, laundry services, swimming pools, etc.

Here are some reasons why you should plan a stay in Chicago’s guesthouses during your next visit;

• Less expensive than hotels but more charming than bread and breakfasts
• They are cozy, family-oriented, and some of the best alternatives to hotels in Chicago
• Guesthouses give you a glimpse into local life in The Windy City
• You can foster a connection with the house owners for a more personalized and authentic stay.

To make sure that the guesthouse is up to your expectations, consider the following:

• Is the location in a quiet residential area or a bustling neighborhood of Chicago?
• What amenities are included (complimentary breakfast, swimming pool, gym, parking, etc.)?
• Does the guest house offer complimentary breakfast?
• What does your room offer? Will you get balconies? Full-size kitchens? Spacious living rooms?
  

8. Glamping In And Near Chicago

Chicago’s hustle and bustle attracts many, but some of the travelers want a much-needed break from that, and glamping sites seem to be the best alternatives to hotels. Retro trailers, glamping sites, cabins surrounded by woods, and aesthetic campsites let you experience nature like nothing else. Some of our favorite glamping sites near Chicago are Vintage 1850’s Log Cabin, Charming Group Glampsite, and Mulln-Heim Vineyards. And if you don’t want to be far away from the city, the Gwen Lux Suite Terrace will let you sleep under the stars on the 16^th floor of the McGraw-Hill building.

Here is why you must choose glamping over hotels in Chicago!

• They are romantic, perfectly secluded, and away from the crowd!
• Chicago has some breathtaking nature around it, and with glamping, you can stay closer to the marshes, dunes, and sandy ridges.
• In winter, you can go ice skating, skiing, and sledding
• Illinois state parks have some of the most aesthetic glamping sides, like treehouses, safari tents, and cabins.

You can always make your glamping experience even more special by considering these points;

• How comfortable are the beds
• What type of bathrooms will you get? (an outdoor heated shower or en suite bathroom)
• Will the accommodation provide you with facilities for cooking food?
• Does the glamping site have electricity and WIFI?

Whether traveling as a family, solo explorer, or a couple, these alternative accommodations in Chicago will curate such an authentic experience for you that you will never look back at hotels again. Want to make more travel memories? Subscribe to our newsletter to avoid wondering, as we have more exciting itineraries planned for you!

Post Views: 12