12 Chicago High Rise Apartments on Airbnb That You Can Rent

In case you didn’t know, Chicago is home to the US’s most impressive architectural feats.

I say that knowing that New York City also has its own list of impressive skyscrapers, that cities like Savannah and New Orleans have impressive colonial structures, and that San Francisco has a balance of many distinct forms, from its Victorian homes to modern business hubs.

But Chicago stands alone when it comes to sheer spectacle, range of projects, and grandiosity.

Even more impressive, its list of innovative, sustainable skyscrapers keeps expanding thanks to new projects like The St. Regis and The Aqua Tower.

And if you’ve been paying attention to my hospitality advice, you know that I always try to book a stay at a hotel or rental that capitalizes on the destination’s overall atmosphere.

In the Windy City, if you want to take a bite out of its lovely architecture, there’s no better way to do so than at one of the many Chicago high-rise apartments spread across the city’s coolest residential skyscrapers.

Forget the architectural tours—as soon as you wake up and roll over, you’ll be treated to an unforgettable bird’s eye view of the city’s top buildings.

Best Chicago high rise apartments on Airbnb that are available for bookings

12 coolest Chicago high rise apartments on Airbnb

Highrise Hideout

Both chic and cozy, this high-rise lets you take a more homey look at life above the 30^th floor. In addition to a gorgeous two-bedroom apartment with floor-to-ceiling windows, you also get perks like a community pool and a swanky fitness center.

Sonder Onterie

As a Sonder product, this is a hotel rental rather than a traditional Airbnb rental. However, if you’re on the hunt for a high-rise Airbnb that absolutely oozes style, the trade-off is worth it. Not only are you in one of the flashiest buildings on the Magnificent Mile, but you also get those hotel-style perks like 24/7 support and housekeeping services.

Kasa Studio

I’ve got three Kasa rentals listed, which offer a (slightly) more affordable way to stay inside a Chicago high-rise. As with Sonder, you get a few hotel-style amenities thanks to the professional management, including a virtual front desk and a choice between different layouts. Plus, the building’s amenities, including a fitness center, pool, and other communal spaces. If you don’t like the studio, check out their larger studio or their one-bedroom below.

Kasa Large Studio. If the original studio is too small, consider renting the larger unit. Just know that this is a two-person stay, despite its slightly larger size.
Kasa 1 Bedroom. This one-bedroom unit lets you sleep three, by contrast. The couch is a pull-out where you can sleep a third.

The Millenium Manor

Located smack in the heart of the Loop, this is one of the coolest Chicago high rise apartments on Airbnb at the moment. That’s thanks to the building’s superior offerings. There’s a pool and a fitness center… but there’s also a small, grassy garden, another deck for lounging, a game room, and even a movie theatre. And you can enjoy it all while surrounded by Chicago’s most impressive skyscrapers.

Downtown #4

This two-bedroom rental is full of character—you’ll notice that it’s more colorful and spirited than its counterparts. If you’re looking for that type of local flair, then book your stay at Downtown #4. Uniquely, this building is also rented by a local college and is used as a campus. But don’t worry—the young students are housed on a separate floor.

High-end 1BR

Want to rent a Chicago high rise that delivers on dramatic, modern views? This one-bedroom apartment is easily one of the swankiest on the list. As an added bonus, it comes with a small balcony, letting you really soak up Chicago’s elevated atmosphere. Even inside, the floor-to-ceiling windows make a strong impact.

Luxury Downtown Chicago

Simple, very chic, and with two bedrooms, this luxury downtown unit is slightly more accessible for anyone traveling in a group. The apartment has plenty of space, along with a massive shared roof where you can hang out. Though there’s no pool, there is a large fitness center.

River North

This two-bedroom stay comes with free parking, letting you drive in without worrying about exorbitant garage fees. It also sleeps six, in case you want to save a bit on nightly rates using the pull-out couch. Plus, you also get a shared rooftop with barbecue grills, along with a separate private balcony in-unit.

River North Private Deck. The same rental management company runs another two-bedroom unit in the same building. This one includes a larger private balcony.

Top-Tier Stay

If you’re on the hunt for lake views versus city views, then this rental unit is unbeatable. Located on the 49^th floor, you’ve got a bird’s-eye view of the city—and beyond. Its floor-to-ceiling windows showcase Lake Michigan, while the building itself (The Summit) is one of the more modern apartments on this list.

The World Tour of Oopsies: Chapter 12—The Horse

[The World Tour of Oopsies is an ongoing series of travel stories about my first decade of travel. During these adventures and misadventures, I had to unlearn many things I thought I knew about life. Welcome to my miseducation.]

Catch up on the World Tour of Oopsies:

Part I / The worst hostel in the world

Last week, I covered one of my favorite adventures from Costa Rica’s Pacific coast at Envision Festival (see: Ch. 11). But Costa Rica is a narrow country with plenty of coastline, and I preferred the more tropical Caribbean coast.

Enter Puerto Viejo, one of the most accessible towns in the province of Limon. It’s a perfect, lazy beach hub for backpackers—and my friends and I loved to visit thanks to those backpacker-friendly prices.

There was one particularly cheap hostel. A place with a few pavilion-style buildings abutting the gorgeous beach, with a basic lounging area and shared kitchen. And, most importantly, a pavilion with hammocks lining the room, each with a corresponding locker.

For just $7, you could rent a hammock and a locker.

The catch? You had to deal with the hostel’s owner, a noisy American, and his staff, who liked to tote around ice luges that they’d use to dispense free shots to women staying overnight.

That’s about as nice and vague as I can be about the hostel, considering it’s still up and running today.

(If you want to stay at a hostel in Puerto Viejo, stick with one of the top five choices.)

Part II / The horse & the bunker

Like you might be able to tell, the hostel is owned by an eccentric. And the hostel, when I visited, had two notable structures.

The first was a small stable where the owner kept a mare and her young colt. The second was a large bunker-style ship that was beached on the shore, which looked formidable and plain, sort of like a military vessel.

On our second night at the hostel, the hostel owner and his friends invited my friends onto the ship to hang out. (Fun fact: I was visiting with five friends, and three of us were named Taylor.)

We hung out for a while until the sun set, then decided to join the guys on the ship. Again, the ship was beached in the sand, making it seem like a slightly more reasonable suggestion to hang out.

(Later, we would find out that the hostel owner had purchased the bunker-style ship in case of the apocalypse. Sort of like a modest Noah’s Ark, I guess.)

On the way there, we passed the stable with the mare and her baby colt. The hostel owner pointed to the colt and said, “Don’t pet him, he’s an $%#hole.”

At which point my ears perked up. You’d think I would be more cautious of wandering into a grown man’s bunker-ship at night (and especially after my experience in Panama; see Ch. 9), but I was zeroed in on that baby horse instead.

The horse didn’t look like a jerk. It was adorable and awkward, with its long legs. At this point in my life, I was also a little bit like the colt; lawless, awkward, and full of energy.

I hung back a few minutes with two of my friends—I think one of them had forgotten something, so we waited for her before heading into the bunker-ship.

Of course, I wandered over to the stable and petted the mare. Much to my chagrin, I’m now forced to admit that I talked a little trash to the colt. Nothing degrading, just a little sass, like something I’d say to a cousin.

But I clearly upset the soon-to-be-stallion because it rocked its head out and bit me.

I won’t tell you where it bit me—just know that the horse had its revenge, and it was very well-played.

Fortunately, it wasn’t the first time I’d been bitten by a creature at night in a foreign country (see: Ch. 1), and the colt wasn’t venomous. Still, I was mortified enough to whip my head towards my friends and shout, “Don’t tell anyone!”

Part III / How am I still alive?

Looking back, it’s hard not to be thankful the colt bit me; it got my adrenaline pumping enough for me to realize that walking into that bunker-ship was not a good idea.

I mean, I did walk into the bunker-ship, desperate to get away from the mare and her spawn, but I was insistent that we leave soon.

That night, I lay on my hammock, embarrassed that I’d been bitten by a horse and deeply preoccupied by whether or not an apocalypse would come and, if it did, whether I’d need to follow a man like this hostel owner into a bunker.

Now, looking back, I think the bites (scorpion and equine) were wake-up calls. I’ll get into that more later on. (Fear not, this isn’t the last time I’ll be bitten during my world tour.)

TL; DR my world tour of travel stories: Some travelers get bitten more than others.

June Tourist Numbers in Vegas Are Down 11.3%—But Is Las Vegas Dead?

Throughout the summer, reports have swirled that Las Vegas is ‘dead’. The Strip is described as empty, along with casinos, sportsbooks, and entertainment venues. Visitors have also slashed spending, according to reports.

Some believe the setback is due to a range of factors, from rising prices in Vegas to the California wildfires, and could be temporary. Other outlets paint a slightly less optimistic picture based on the expertise of long-time Vegas staff.

Regardless of the reasons why, the data from the Las Vegas Convention and Visitors Authority is clear: the number of visitors is smaller than it was last year, and these visitors are spending less than their 2024 predecessors.

What’s behind the Las Vegas tourism slump?

According to the LVCVA, one reason that tourism numbers are down in the city is due to anxiety around the economy, which means consumers are spending less.

That’s an obvious note here: Vegas is designed for no-holds-barred vacations where just about any delight is allowed… at a premium price, of course.

In short, that type of indulgent vacation is the first to get axed by Americans who are worried about their savings account.

On top of decreased spending from domestic visitors, Las Vegas is also facing a downturn in Canadian tourists and other international visitors. As per Emily Stewart’s reporting for Business Insider, fewer tourists are coming from Asia, and even California, where some are still recovering financially from this year’s devastating wildfires.

Additionally, LVCVA also noted Las Vegas’s increasingly exorbitant prices. Like I’ve mentioned multiple times when covering Vegas, the city has pivoted away from being an after-dark mecca for naughty activities and toward a more welcoming and general entertainment hub.

It’s lost its specific Sin City appeal while also boosting prices, which hasn’t gone over well with tourists.

10 European Cities That Want Tourists Like You to Visit

It’s been a tough year for tourists heading to Italy, Spain, and Portugal.

These three popular Mediterranean destinations have been facing waves of anti-tourism sentiments. After years of unsuccessfully appealing to city authorities to change hospitality-facing regulations, angry locals turned their attention directly to tourists.

Some were beamed with water guns. Others were cornered at calm cafes.

And many were left wondering whether they’d made a huge mistake shelling out thousands to visit popular but suddenly tourist-hating European destinations.

Here’s my take as a permanent resident of Spain who has lived in Barcelona for seven years: anti-tourism sentiment in these locations has been building for a long time, and is now being compounded by a new wave of digital nomads who arrived on legal working visas. Words like gentrification have entered the chat.

There’s no quick fix to the issues brought on by a decade (or more) of mass tourism, in other words. Governing bodies need to make impactful regulatory changes to shift the sentiment towards tourists, in my opinion.

So, if you’re a little sensitive to a place’s ‘vibe’, then I highly suggest visiting another location in Europe.

For example, places that aren’t as suspicious of outsiders and don’t overcharge for everything. Cities where temperatures don’t soar into the 90s or higher. Attractions where the crowds don’t block the view and leave you prone to pickpockets. Areas where locals might even be happy to show off their hometown.

Sounds like a fairytale, right? In reality, you can find locations like these all around Europe. I’ve done a bit of heavy lifting for you based on the last seven years of traveling around the continent.

These are 10 European cities that want tourists like you to come say hello. I’ve also included a few countries, where applicable.

10 European cities that want tourists like you to visit

Cantabria, Spain
Bucharest, Romania
Tbilisi, Georgia
Copenhagen, Denmark
Graubünden or Grisons, Switzerland
Brussels, Belgium
Krakow, Poland
Bulgaria
Wales
Finland

10 European cities that want tourists (plus, 3 countries)

Cantabria, Spain

In an act of defiance, I’m recommending a Spanish destination straight off the bat. Cantabria is a Northern, coastal province known as ‘Little Switzerland’ thanks to its gorgeous mountains.

Located west of Pais Vasco or Basque Country, it also puts you in proximity to cities like Bilbao. It’s also home to the Cave of Altamira, one of Spain’s 12 National Treasures, and locals who (probably) don’t own any water guns.

Here’s where to stay and what to do in Cantabria.

Bucharest, Romania

Romania is enjoying a travel boom thanks to domestic European interest in visiting. From backpackers to ravers, Bucharest has started to attract tourists who want a grittier and more authentic travel experience. (I’ve heard it likened to Berlin twenty years ago.)

Aside from authenticity, Bucharest is also known for its lovely Belle Epoque architecture, and is even home to the world’s second-largest building, the Palace of the Parliament.

Here’s where to stay and what to do in Bucharest.

Tbilisi, Georgia

Similar to Bucharest (and Bulgaria, below), Tbilisi is full of life—and locals are passionate about showing off their city. Expect exciting new projects, from vinyl stores to lounges to art galleries.

In Tbilisi, you also have tons of history to enjoy, as it’s one of Europe’s oldest capitals, with a staggering 15 centuries of traditions to dig into. Also, the mountains surrounding the city are dramatic and absolutely gorgeous.

Here’s where to stay and what to do in Tbilisi.

Copenhagen, Denmark

If you read my recent piece on Copenpay, you might already know that Copenhagen, the capital of Denmark, has a solid tourist program. You just show up, contribute a little bit to the city, and then reap a reward that’s proportionate to your service.

That should clue you in: Tourists are very welcome in Copenhagen, so long as they respect the city and keep the noise and riff-raff down. In exchange, you get to experience lovely townhouses and canals, a clean and sustainability-focused city, and iconic landmarks like the Little Mermaid.

Here’s where to stay and what to do in Copenhagen.

Brussels, Belgium

Everyone skips out on Brussels because it’s known as the ‘Capital of Europe’ and, by default, dubbed a boring city. That’s because Brussels is home to major headquarters, including both the EU and NATO.

That gives parts of the city a sterile, DC-like feel—but that’s hardly the end-all. Do you like chocolate and pastries? You’ll love Brussels. What about walkable, charming neighborhoods? Once again, you’ll love Brussels.

Here’s where to stay and what to do in Brussels.

Krakow, Poland

Krakow offers an unspoiled look into Poland’s long past, and especially its Medieval era. Much of the city was spared from destruction in WWII, giving you a front-row seat to places like the Wawel Castle and Wawel Cathedral—two places that I won’t forget visiting.

The former has a massive interior gallery that feels like something out of a dream or a fairytale storybook. I think ‘fairytale’ is a great way to describe Krakow in general. Like Wales and Catalonia, the city also has a thing for dragons.

Here’s where to stay and what to do in Krakow.

Graubünden or Grisons, Switzerland

If you can foot the bill to Graubünden, Switzerland’s largest province (aka a canton), you’ll be treated to the world’s most stunning Alpine views.

And while you might be thinking about a winter visit, know that Graubünden is just as gorgeous in the summertime, offering cool temperatures and unbeatable hikes. Plus, those hefty prices drop in summer, letting you avoid hiked prices and crowds.

Here’s where to stay and what to do in Graubünden.

Bulgaria

Bulgaria is yet another Eastern European country that is (incredibly) open to tourists. The capital city of Sofia is a feast for the eyes, and home to enough historic sites to keep you busy for a few days.

But I want to highlight one of Europe’s coolest and least-covered landscapes: the Black Sea. Bulgarian towns like Sozopol and Nessebar are home to ancient architecture… along with lovely beaches that come alive with summer festivities.

Forget the busy beach towns in the Mediterranean—Bulgaria’s Black Sea seaside resort towns have a more magical adventure in store for you.

Here’s where to stay and what to do in Bulgaria.

Wales

Looking for an escape from England? Head to Wales for rugged coastlines and mountains, and plenty of national parks. Many are home to historic castles; there’s an even ‘Iron Ring’ of well-known sites, including Harlech and Beaumaris.

Wales is also a great spot to head if you like history and folklore, as Welsh mythology usually flies under the radar compared to English and Scottish tales. Personally, I’d head straight to Anglesey…

Here’s where to stay and what to do in Wales.

Finland

Which European cities want tourists to visit the most? Helsinki has to be one of them. Why is that? I’m rounding off my list with Finland—which is famously the world’s happiest country.

Given its northern location, Finland hasn’t been overrun with tourists. Whether you want to visit Santa Claus in the Arctic Circle or simply explore Europe’s northernmost capital city, you’ve got choices. Just make sure you arrive prepared if you’ll be experiencing Finland in winter.

Here’s where to stay and what to do in Finland.

5 Types of Luggage Bags in Order of How Necessary They Are

Most travelers have a solid carry-on bag in their arsenal… but what else do you need when it comes to different types of luggage?

Can you really skate by with just a carry-on? Should you also have a reliable check-in just in case? And what about types of luggage like weekender bags, backpacks, and duffels?

You’ve got questions, I’ve got suggestions. Here’s what I’ve learned about the most popular types of luggage over almost two decades of travel. The pieces listed below are ranked in order of how likely you are to use them, and how often.

Let’s explore.

Types of luggage bags in order of how much you’ll need one

Luggage #1: Carry-on

Your carry-on is your best friend. This should be your go-to luggage for just about any adventure. Even if you’re heading out on a two-week escape, I recommend trying your best to stick to a carry-on. It’ll be easier to lug around if you have any other trips scheduled, including domestic flights and train rides.

I have a few suggestions when it comes to picking a great carry-on. First, pay attention to weight—the lighter, the better. Second, pay attention to size. Many airlines are shrinking their carry-on size limits, so the more conservative you are, the better. Check out my favorite carry-ons.

Luggage #2: Check-in

I try to avoid checking luggage unless I’m traveling a long distance and/or for more than two weeks. That being said, I usually prefer check-ins for winter trips. My partner and I will forego the carry-ons to check luggage together. It gives us the room we need to stuff in sweaters, big socks, hats, etc.

My favorite check-in piece is the Carl Friedrik Carry-On; if you can swing it, it’s well worth the added price. Its wheels and overall construction are sexy-sleek, while its casing is shockingly lightweight. If not, check out other great check-ins; as with carry-ons, look out for lighter types of luggage.

Luggage #3: Backpack

Backpacks—a type of luggage so famous that a whole genre of travelers took its name. But what about travelers who wouldn’t call themselves backpackers—should you also have a Cotopaxi or REI bag in your closet?

Personally, I don’t think backpacks have any usage beyond being hyper-portable and prepared to weather the elements. So, if you’re not an adventurer who likes to get out into the wild or a backpacker who’s always eyeing the next horizon, no need to go for a backpack.

Luggage #4: Purse, tote bag, & duffel—aka Weekenders

Below, I’ll cover weekender bags. Before the concept of a weekender bag emerged, there was the humble purse or tote bag. These are larger bags designed for multi-day use, with one exception. Unlike other types of luggage listed here, purses and tote bags aren’t always marketed towards travelers.

Here’s my point: just because a piece isn’t listed as a travel bag or luggage, that doesn’t mean you can’t use it. For example, the CALPAK offers travel-ready bags like its Expandable Laptop Tote and its famous Luka Duffel. You could use either for travel or for a day out on the town.

Those two CALPAK pieces linked above both work great for weekend trips, and are often lauded as some of the best picks out there. They have a compartment for shoes, a laptop sleeve, and other features that highly mobile travelers usually look for.

Just know that not every weekender bag is going to be billed as such; some are simply dubbed duffels, while others might be listed as ‘carryalls’.

Now onto the big question—do you actually need a weekender in your closet?

I would personally get more use out of a weekender bag than a backpack because I’m no longer in my off-road adventuring era. That being said, I have an over-the-shoulder, oversized pink tote that I use as a weekender. I didn’t need to make a separate purchase to get weekender capabilities, in other words.

That being said, if you’re someone who tends to ravel for the weekend more often than not (even if it’s not to go on vacation but, say, visit family), then invest in a solid weekender. I’m a CALPAK fan, so I highly suggest looking into the pieces linked above.

Luggage #5: Duffel

Small duffels can be used as weekenders—but what about larger travel-specific duffels? Is there any reason you’d want to have a large bag with zero rolling capabilities?

I’ve personally used these types of shapeless, massive duffels for moving purposes, having spent my twenties living in a range of cities. They were perfect for stashing items of all shapes and sizes.

But there are many types of duffels out there—including rolling duffels.

If you’re packing to the brim and want to toss in items of any shape/size, a duffel is a great option. On top of rolling duffels and oversized duffels, you can also find pieces made from thin materials, which means they pack down into a small shape, just like a barely-there tote.

Here’s my verdict: there’s no need to overspend on duffels, but you might want a hardy, shapeless one on your side if you’re moving to another city or, by contrast, a duffel you can fold up and stash if you don’t need it for your whole trip.

Want a look at the sheer range available to you? Just start with Vera Bradley.

Venice Enforcing 7 ‘Forbidden Behaviors’ for Tourists That Come with Fines

In 2024, the City of Venice laid out new rules for incoming tourists, limiting group size, enacting day-trip fees, and more.

Similar to the new regulations that launched for Machu Picchu in 2025, the new rules seek to minimize the impact of high-volume tourism. In both cases, it’s designed to protect major sites.

But in the case of Venice, those new regulations are also designed to improve the daily lives of local residents. Along with protecting major landmarks, authorities in Venice are zeroing in on city culture in the hopes of improving tourist behavior.

While I’m sure this has been on the authorities’ radar for a while, this year’s highly publicized Jeff Bezos wedding (which was planned to be in the city center) was the source of city-wide protests. Locals were so thorough that the wedding was eventually moved.

And now, it looks like local authorities are cracking down on rules aimed at tourists, dubbed ‘Forbidden Behaviors’.

What are the new rules for tourists in Venice?

Technically, the rules aren’t new since they’ve been around since 2022—only the vigor with which they’ll be policed. For years now, local groups have been looking for ways to meaningfully improve tourist behavior.

For example, back in January 2024, Città di Venezia released a list of 12 norms, called ‘good rules for the responsible visitor’. The list includes suggestions on how to have a great trip while being a respectful tourist, from exploring islands across the lagoon to visiting artisan workshops to walking on the right-hand side of the street.

It’s a respectable list—but you won’t face any fines for deviating. That’s not the case with the newly enforced forbidden behaviors, which come with fines and being banned from the location.

Here’s what not to do in Venice:

Don’t eat and drink sitting on the ground, bridges, steps, walkways, etc. (Fine: €100-200)
No swimming or diving into the canals (Fine: €350)
Don’t litter or leave out trash bags in public areas (Fine: €350)
Don’t walk around in a swimsuit (or bare-chested) (Fine: €250)
Don’t feed pigeons or seagulls (Fine: €25-250)
No bicycles—even if you’re walking them by hand (Fine: €100)
No camping in public areas (Fine: €200)