fbpx

Where to Stay in Chicago: The Best 12 Chicago Airbnbs

where to stay in chicago

Any Chicagoan will tell you that The Windy City is abundant with hidden gems. With Chicago’s booming social scene, you want to make sure you see more than Navy Pier and The Magnificent Mile on Michigan Avenue.

Knowing what to do is as equally important as knowing where to stay in Chicago. Similar to the scene of New York City, it’s bursting with a diverse set of neighborhoods, and each area offers something unique to travelers from all walks of life.

In former years, Chicago’s historic South Loop was a catalyst for Chicago tourism. Now, locals and tourists alike are traveling to Chicago neighborhoods with a little more zest like Wicker Park, Old Town, Bucktown, Chicago River North, and Lincoln Park.

As far as where to stay in Chicago, the Near North Side and North Side is your best option if you want an authentic Chicago experience. Here, you’ll discover the best of the city, including restaurants, bars, and entertainment.

I’ve searched through all of Chicago’s Airbnbs to find the best places to stay in Chicago, based on price, aesthetic and style, and location.

Booking an Airbnb for the first time? Be sure to use my referral link to get $40 off your booking!

Where to Stay in Chicago: Best Chicago Airbnbs

1. Sophisticated Flat in Historic Building

where to stay in Chicago

This Instagram-worthy Airbnb Plus is located in Chicago’s Old Town. Guests are just miles away from Lake Michigan and classic Chicago activities such as Second City, which schooled famous SNL comedians like Amy Poehler.

The neighborhood itself is quite dreamy with Victorian-style homes. It’s the perfect staycation spot for a little bit of romance or to treat yourself to a charming urban-getaway.

Up to 2 guests // 1 bedroom // 1 bed // 1 bath. Prices from $120 per night. Check pricing and dates here.

2. Beautiful Loft Style Apartment

where to stay in Chicago

This second space is the perfect accommodation for large groups. Multiple guests return to this loft because it’s clean, accessible, and family-friendly!

Located in Lincoln Park, this Airbnb Plus is near the Peggy Notebaert Nature Museum and the Lincoln Park Zoo, and the zoo is free admission. These hot spots are bustling with family-days and special events for adults.

Note: The loft bedroom requires the use of a ladder and is only three-feet high. Fun for kids or slumber parties!

Up to 8 guests // 2 bedrooms // 2 beds // 2 baths. Prices from $112 per night. Check pricing and dates here.

3. Enjoy Chicago’s Nightlife from a Studio Apartment

where to stay in Chicago

This cozy and bright Airbnb Plus is the perfect solution for a weekend getaway.

Located in Uptown, it’s in a central location where guests can easily walk to the red line (the main train line) or Lake Michigan. Additionally, this space is just a few miles away from Wrigley Field and Wrigleyville, home to the Chicago Cubs, and a vibrant nightlife.

The apartment is above a bar, which can get pretty lively at night. For the right type of guest, this is the perfect crash-pad for an adventure on Chicago’s north side!

Up to 2 guests // studio // 1 bed // 1 bath. Prices from $80 per night. Check pricing and dates here.

4. Contemporary Chic Apartment

where to stay in Chicago

For large groups that don’t know where to stay in Chicago on a budget and in a comfortable space, then this next location is for you!

Considering the size of this trendy and well-lit apartment, the price is an absolute steal for a large group. This pristine Airbnb Plus is ideal for guests who prefer a spacious apartment.

Public transportation is nearby making it easy to get to the best restaurants and entertainment in Chicago.

Up to 10 guests // 3 bedrooms // 5 beds // 2 bath. Prices from $60 per night. Check pricing and dates here.

5. Modern Apartment in Bucktown

where to stay in Chicago

Any city-dweller can appreciate an apartment with a picturesque kitchen like the one in this Airbnb Plus! The entire space is great and the location is prime.

Bucktown’s up-and-coming-scene is the “New Lincoln Park.” However, this gem of a neighborhood is uniquely its own with a vibrant hub of culture.

The location is perfect for anyone who wants to explore indie boutiques, trendy cocktail bars, and restaurants. This modern apartment is located in a quiet location, but close enough to Bucktown’s upbeat social life.

Up to 4 guests // 2 bedrooms // 2 beds // 1 bath. Prices from $95 per night. Check pricing and dates here.

6. Modern Apartment Near the Boystown Nightlife

where to stay in Chicago

The artistic and bright decor in this flat reflects the liveliness of the neighborhood!

The apartment is situated in Boystown, one of the largest LGBT communities in the United States. This place is perfect for an energetic crowd that wants an unforgettable Chicago experience.

Bring your dance moves, because this location is just a brief walk from the most popular dance spots in Chicago!

Up to 4 guests // 2 bedrooms // 3 beds // 1 bath. Prices from $104 per night. Check pricing and dates here.

7. High-Rise City Pad

where to stay in Chicago

This stylish West Loop pad sits high above the city for those who want a chic stay in Chicago. The apartment is smaller but it has all the amenities needed for a comfortable stay.

Previous travelers love the convenience of the location. The apartment is central, which makes it easy for guests to head downtown and explore Chicago’s myriad of restaurants and entertainment.

Up to 3 guests // 1 bedrooms // 1 beds // 1 bath. Prices from $139 per night. Check pricing and dates here.

8. Light Filled Loft Apartment near Downtown Chicago

where to stay in Chicago

If you want your stay to be close to the airport, look no further than this colorful and spacious apartment! Besides being close to the airport, this apartment is a short train ride to Wicker Park.

This Airbnb Plus is surrounded by countless restaurants, coffee shops, clubs, indie stores, and entertainment, all within walking distance.

Up to 3 guests // 1 bedroom // 1 bed // 1 bath. Prices from $113 per night. Check pricing and dates here.

9. Light Filled Loft Apartment near Downtown Chicago

where to stay in Chicago

This bright and clean Airbnb Plus is a dream apartment! Situated in a vintage greystone building, this place has everything you need to enjoy a comfortable stay.

The historic surrounding community has something for everyone; contemporary restaurants, bars, and shops. For history enthusiasts, it’s a great location to discover homes and businesses as old as the city itself.

Up to 4 guests // 1 bedroom // 2 beds // 1 bath. Prices from $130 per night. Check pricing and dates here.

10. Spacious Apartment in Wicker Park

where to stay in Chicago

If you’re traveling with a group of four or more, and want to stay in an apartment with that classic city feel, then this is the spot for you!

The large windows, the sleek floors, and the modern style is only a part of what makes this apartment prime. This stylish pad is within walking distance to some of Wicker Park’s most trending spots.

Up to 7 guests // 2 bedrooms // 4 beds // 2 baths. Prices from $100 per night. Check pricing and dates here.

11. Contemporary Studio with City Views from Terrace

where to stay in Chicago

This Airbnb is accommodations goals! Here, guests can enjoy all the beautiful amenities including a shared terrace adorned with lights.

If you want to hang out like a Chicagoan, you’ll want to grab a few drinks and spend time on this beautiful rooftop with a city view.

The apartment itself is a cozy, dreamy Italian-inspired space. Perfect for a romantic weekend getaway or solo travel.

Up to 2 guests // studio // 1 bed // 1 bath. Prices from $107 per night. Check pricing and dates here.

12. Honeycomb – Private Terrace with City Views

where to stay in Chicago

Within the heart of the trendy River North is this modern apartment perfect for groups of up to three.

The apartment is close to some of Chicago’s most popular cocktail bars, including Three Dots and a Dash, a tropical speakeasy, and Celeste, a swanky art deco cocktail bar.

Up to 3 guests // 1 bedroom // 1 bed // 1 bath. Prices from $159 per night. Check pricing and dates here.

That’s my list of where to stay in Chicago! If you book one of these Airbnbs, tag me in a pic or Insta Story and show off your Chicago Airbnb. Happy travels!

Planning a trip to Chicago? Be sure to check out my Chicago Travel Guide!

Submit a Comment

You have successfully signed up!

Pin It on Pinterest

Apple Hill: All the Best Apple Hill Stops

Apple Hill: All the Best Apple Hill Stops

I grew up in El Dorado Hills, a small town in between Sacramento and Tahoe, and Apple Hill was a popular destination for elementary school field trips. But you know what's crazy? I hadn't been to Apple Hill since I was a kid! I've been wanting to go back for years to...

Best Restaurants in Cinque Terre

Best Restaurants in Cinque Terre

  We had some seriously delicious food in Cinque Terre, but we also went to a couple places that ended up being touristy and bland (with crappy service to boot). You won’t find those places on this best restaurants in Cinque Terre list, and frankly we were led there...

Four Seasons Seattle Review

Four Seasons Seattle Review

Our recent stay at the Four Seasons Seattle was so, so dreamy. This luxury, 5-star hotel is in a prime location in Downtown Seattle, right by the waterfront. Every detail, from the service, to the afternoon treats in the lobby, were just lovely. Read on for my full...

38 Different Things to Do in London + Everywhere to Eat and Drink

38 Different Things to Do in London + Everywhere to Eat and Drink

Five months after my London trip, I am finally getting a travel guide up for this incredible city! I was living there for a month and a half for work earlier this year and it was my first time in London. I absolutely fell in love with it! There are so many different...


Coffee Break

Coffee Break

I cannot wait to start putting out some of my Cinque Terre content!! It's seriously one of the most beautiful places I've ever seen. Until those travel guides and other Cinque Terre posts are ready to go later this month, here's an outfit look from one of our days...

Coffee Break

Coffee Break

I cannot wait to start putting out some of my Cinque Terre content!! It's seriously one of the most beautiful places I've ever seen. Until those travel guides and other Cinque Terre posts are ready to go later this month, here's an outfit look from one of our days...

Tieks Shoes: My go-to flats for traveling the world

Tieks Shoes: My go-to flats for traveling the world

Whenever I’m packing my bags, no matter where I’m going, you can always count on there being at least one pair of Tieks shoes in my luggage (but usually two or three, because you know…a girl’s gotta have options!). When I worked at an office, I wore Tieks almost every...

Clothing Packing List for Europe Summer Vacay

Clothing Packing List for Europe Summer Vacay

I just got back from spending a month in Italy and even though it was just barely into June by the time I left, Europe was getting HOT! 🥵 Today I'm partnering with Ibotta to share a packing list for Europe and all the clothes you'll want to pack in order to beat the...

Palm Springs Desert Outfit

Palm Springs Desert Outfit

I visited Palm Springs for the first time earlier this year, and of course I had to shoot with the iconic windmills! We were also running around checking out all of the Desert X art installations. The art installations are over now, but hopefully they'll be back with...

Tieks Shoes: My go-to flats for traveling the world

Tieks Shoes: My go-to flats for traveling the world

Whenever I’m packing my bags, no matter where I’m going, you can always count on there being at least one pair of Tieks shoes in my luggage (but usually two or three, because you know…a girl’s gotta have options!). When I worked at an office, I wore Tieks almost every...

Jade

Jade

I wore this cute weekend outfit during our recent weekend trip up to Santa Rosa. I love the print on this fun little wrap dress, and while I don't usually wear a lot of green, I love the shade of this dress. The ruffled sleeves and hemline add a sweet touch, and I...

Palm Springs Desert Outfit

Palm Springs Desert Outfit

I visited Palm Springs for the first time earlier this year, and of course I had to shoot with the iconic windmills! We were also running around checking out all of the Desert X art installations. The art installations are over now, but hopefully they'll be back with...


Custom skincare with Curology

Custom skincare with Curology

Finding the right skincare routine for yourself can be really hard. I know I've done a lot of trial and error to figure out which beauty products work for me and that my skin reacts well to. And the "error" part of the trial and error is always the worst. Like, hi...

Taiwan Beauty Products

Taiwan Beauty Products

Taiwan Beauty Products When I was in Taipei recently, my friend Francesca was showing me some of the Taiwan beauty products and other Asian beauty trends that are popular there. I love checking out new beauty products and trends, especially ones that we can’t get here...

Custom skincare with Curology

Custom skincare with Curology

Finding the right skincare routine for yourself can be really hard. I know I've done a lot of trial and error to figure out which beauty products work for me and that my skin reacts well to. And the "error" part of the trial and error is always the worst. Like, hi...

How to fix damaged hair in a snap

How to fix damaged hair in a snap

This is a sponsored conversation written by me on behalf of Pantene. The opinions and text are all mine. This winter's harsh weather, combined with lots of heat styling for holiday parties, events, and photo shoots has done a number on my hair. Whenever I have dry...

How to fix damaged hair in a snap

How to fix damaged hair in a snap

This is a sponsored conversation written by me on behalf of Pantene. The opinions and text are all mine. This winter's harsh weather, combined with lots of heat styling for holiday parties, events, and photo shoots has done a number on my hair. Whenever I have dry...

Sunday Funday

Sunday Funday

Flamingos make everything more fun, amirite? Last weekend before I headed out on a biz trip to Canada Omied and I had a little Sunday Funday date day in the city together. I'd been dying to check out a new Cuban place in the Mission, which is officially the most...

Turning Point Spa

Turning Point Spa

Getting regular facials and have a great aesthetician (or two!) that you can rely on is a super important part of your skincare routine. I recently got to visit Turning Point Spa in Marin, and had such a lovely experience. The owner, Laurence McKee, is a...

Très Sleek: Smooth and Brilliant with Revlon Hair Tools

Très Sleek: Smooth and Brilliant with Revlon Hair Tools

This post was sponsored by Revlon Hair Tools as part of an Influencer Activation for Influence Central and all opinions expressed in my post are my own. Très Sleek: Smooth and Brilliant with Revlon Hair Tools: I’ll be honest, I’m good at many things, but doing my own...

Tieks Shoes: My go-to flats for traveling the world

Tieks Shoes: My go-to flats for traveling the world

Whenever I’m packing my bags, no matter where I’m going, you can always count on there being at least one pair of Tieks shoes in my luggage (but usually two or three, because you know…a girl’s gotta have options!). When I worked at an office, I wore Tieks almost every...

Date Night Makeup: Pretty Fall Neutrals

Date Night Makeup: Pretty Fall Neutrals

Today I’m sharing my go-to makeup look this fall for a night out. Whether it’s a date night with my hubby or my girlfriends, these are the products I keep reaching for and the earthy neutrals I’ve been incorporating into my beauty looks. And to make things super...

Three self-care skincare routines you haven’t tried

Three self-care skincare routines you haven’t tried

This post has been sponsored by Cetaphil®. All thoughts expressed are my own. Skincare has always been something I’ve had to spend a lot of time (and money...and trial and error) on. My teenage years were spent being acne-prone, while my twenties involved a lot of...

No Heat Beach Waves Hair Tutorial

No Heat Beach Waves Hair Tutorial

This shop has been compensated by Collective Bias, Inc. and its advertiser. All opinions are mine alone. #BeBeachBlonde #CollectiveBias People always ask me how I keep my long hair so healthy. My biggest tip is that I rarely use heat on it. My hair dries...

Très Sleek: Smooth and Brilliant with Revlon Hair Tools

Très Sleek: Smooth and Brilliant with Revlon Hair Tools

This post was sponsored by Revlon Hair Tools as part of an Influencer Activation for Influence Central and all opinions expressed in my post are my own. Très Sleek: Smooth and Brilliant with Revlon Hair Tools: I’ll be honest, I’m good at many things, but doing my own...

Bridesmaid Makeup

Bridesmaid Makeup

I spent this past weekend in North Carolina for my beautiful cousin's wedding. It was such a fun-filled weekend and I'm missing all the family time already! I was honored to be a bridesmaid, and I brought along my new EcoTools hair and makeup brushes to keep my...

Taiwan Beauty Products

Taiwan Beauty Products

Taiwan Beauty Products When I was in Taipei recently, my friend Francesca was showing me some of the Taiwan beauty products and other Asian beauty trends that are popular there. I love checking out new beauty products and trends, especially ones that we can’t get here...


What to wear to an Indian Wedding

What to wear to an Indian Wedding

Last month a dear friend of mine from grad school got married. Both the bride and groom are Indian, and since we'd been to an Indian wedding before we semi-knew what to expect—beautiful, colorful outfits, a morning ceremony and evening reception, and tons of delicious...

Desenio Review: Cute Art Prints at Reasonable Prices

Desenio Review: Cute Art Prints at Reasonable Prices

I've been incorporating a little bit more home decor posts into my blog over the last year or so, and it's been so much fun to shoot and share that kind of content with you guys. While I definitely can't wait til we own our first home some day (and allll the...

Pumpkin Quinoa Breakfast Recipe

Pumpkin Quinoa Breakfast Recipe

My favorite part of the day is waking up early in the morning and heading straight to the kitchen to make my coffee and breakfast. I love mixing it up every morning with either something savory or sweet! I've recently found a new love for quinoa and I can't stop...

Woman Crush Wednesday: Kara Harms, Founder of Whimsy Soul

Woman Crush Wednesday: Kara Harms, Founder of Whimsy Soul

I'm so excited to be continuing with my Woman Crush Wednesday series, where I'm interviewing and featuring bad-ass boss babes! Today we're chatting with Kara Harms, the founder and editor behind the travel and lifestyle site, Whimsy Soul. When Kara and I first met...

Fall Bucket List

Fall Bucket List

Fall is officially here and it's finally starting to feel like it in San Francisco too! I'm ready for the change in season and have been loving the crisp air and cooler weather. I feel like each season passes so quickly (I mean, they're only three months long, which...

Wedding Wednesday: Menguin

Wedding Wednesday: Menguin

MENGUIN UNBOXING VIDEO & REVIEW  Back when we were planning our wedding (which was already 8 months ago! I can't believe it.), I did a post about Menguin, the suit rental company we were using for our groomsmen's looks. Our groomsmen looked so handsome in their...

Five Ways to Add More Storage to Your Kitchen

Five Ways to Add More Storage to Your Kitchen

We live in a one bedroom apartment in SF and our kitchen situation is very small—like, it feels crowded if there are two people in the kitchen, small. Since we have such limited space in our kitchen, I've found a few items over the years from Wayfair to help optimize...

Sweet Corn Soup Recipe

Sweet Corn Soup Recipe

There's nothing better than making a delicious, warm bowl of soup during the fall when the weather is cool and the air is crisp. I love all things corn and nothing screams comfort food more than corn soup! I love the idea of incorporating sweet and savory, which is...

Woman Crush Wednesday: Lindsay Kinder, founder of Food La La

Woman Crush Wednesday: Lindsay Kinder, founder of Food La La

You guys!! I am SO freaking thrilled to be starting a brand new content series on What The Fab today. It’s Woman Crush Wednesday, where I’ll be sharing Q&A-style interviews with bad-ass female entrepreneurs who are paving their own way, founding their own...

Fall Bucket List

Fall Bucket List

Fall is officially here and it's finally starting to feel like it in San Francisco too! I'm ready for the change in season and have been loving the crisp air and cooler weather. I feel like each season passes so quickly (I mean, they're only three months long, which...

How to plan the perfect wedding timeline

How to plan the perfect wedding timeline

This post could also be titled, "How to project manager the shit out of your wedding." ;) Over the last year while we were planning our wedding, I've had several coworkers and friends get engaged too. They've all asked for the wedding run of show (fancy event-planner...

Five chic ways to add some fall home decor to your life

Five chic ways to add some fall home decor to your life

  Who else is excited for fall?? I feel like summer just flew by, so I plan to embrace the fall season and really soak all the fall vibes up, in an effort to slow down and savor the season. I'm starting with adding some fall touches to my home. In my opinion,...

Pumpkin Spice Coffee: A Latte Recipe

Pumpkin Spice Coffee: A Latte Recipe

PSLs are so popular this time of year, and I feel like Starbucks starts bringing back their pumpkin spice lattes earlier and earlier every year. I love pumpkin so I'm ok with it! And even though people call PSLs basic, sometimes things are basic for a reason—they're...

September, Instagrammed

September, Instagrammed

Trying to only mildly freak out that it is officially Q4 of 2019! When I started writing the title for this post, I accidentally wrote, "August, Instagrammed," because I just can't believe that we're already in the month of October. But it's ok, I'm ready for the...

Blushing

Blushing

 I absolutely loved wearing this pretty blush Marchesa gown for my friend's wedding a couple months ago. She had her bridesmaids all pick out long dresses in either blush or champagne, and the colors and looks all came together beautifully. This particular dress...

Decorating our home with canvas prints from Mixbook

Decorating our home with canvas prints from Mixbook

Happy Monday, y'all! I'm so excited to share something special I've been working on with Mixbook today! You're likely already familiar with Mixbook and know about their beautiful and easy to create photo books, but did you know that they also do custom home decor...

Spiced Cider with Rum Recipe

Spiced Cider with Rum Recipe

It's finally starting to feel like fall in San Francisco and I'm so excited! Just last week we had a heat wave come through and since nobody has AC, we were all sweating. But just a week later, there's a crispness in the air and things are downright chilly (for...

My Secret to Taking Better Care of Myself

My Secret to Taking Better Care of Myself

This post has been sponsored by Cetaphil®. All thoughts and opinions are my own. By this time of year, any talk about new year’s resolutions has completely died down. No one is posting on social media asking how you’re doing with sticking to your resolutions because...