6 Best Hotels with Pools in the Room in Chicago

Chicago, in its entirety, might go into hibernation during the biting winter, but it’s a different story when the weather turns. The fun-loving city-goers, besides travelers like us, come out in full force during the much-anticipated summer months when the weather is great. After all, Midwestern summers are hard to beat, as there are special events, street fairs, and so many festivals virtually every weekend. However, there’s also the sweltering humidity and stifling heat, which we had a way to beat – luckily. We’re talking about getting Chicago hotels with pools in the room! What’s more, we found options for not just hotels across all budgets but also B&Bs. Now, pools might be a stretch, as pools for us also include bathtubs and jacuzzis; after all, they’re also perfect to beat the heat, aren’t they?

In the end, getting pool rooms was one of the best reprieves for beating the heat, as the last thing we wanted to do was hide out in the air conditioning. So, whether you’re a local planning a staycation or a traveler from out of town, a pool or a jacuzzi in Chicago is never too far off whenever you want to cool off. Here’s a useful guide to the Windy City’s hotels with pools in the room to fight off that summer sweat in style.

Villa D’ Citta

6

Best B&B. We were on the lookout for a non-hotel with a unique pool or bathtub feature when we miraculously stumbled upon Villa D’Citta. Tucked in the heart of the shopping and dining district of Lincoln Park, this modernized Chicago B&B offered not one but two options for digs, which had a bathtub/jacuzzi tub right in the room, but with a twist. The first was the suite with the terrace, which boasted a private terrace with access to a sun deck, which had a circular hot tub. But that’s not all. The deluxe queen suite also had a gorgeous marble bathtub in the room, with two steps leading up to it – we felt like modern Roman royalty! What’s more, both rooms had mod-cons like flatscreen TVs, sitting areas, and even fireplaces – this is Chicago, after all.

The Italian-inspired decor of the B&B’s rooms extends to the rest of it too, with large windows with great neighborhood views and well-kept old-timey decor. Our days began with a fabulous continental breakfast every day, and we even had access to the gourmet kitchen if we wanted to whip something up. Are you here on the weekends? There’s a hot breakfast awaiting you. We loved borrowing the bicycles for rent on the property and heading off to explore the lovely neighborhood. The sun-kissed cobblestoned courtyard was another favorite, where we’d soak up the sun on mild Chicago mornings. It’s no wonder that it’s one of Chicago’s most romantic hotels.

Best Western Plus O’Hare International South

5

Most value for money. It’s hard to beat a Best Western hotel when it comes to its rooms and amenities, and the Best Western Plus O’Hare International South is no exception. Tucked in Franklin Park, Illinois, it lies just five minutes away from O’Hare International Airport.

So, when we were looking for a relaxing stay at the end of a long Chicago vacation, this BW outpost seemed perfect, especially since it offered jacuzzi rooms! We aren’t kidding; our king room with a hot tub was not just spacious but even had a huge hot tub right in the room. Located just a few steps from the bed, it even had a separate wet section so the room flooring and carpet wouldn’t get wet. We loved the thought that went into it, as well as the other features in the room, which included a tea/coffee maker, a flat-screen TV with cable channels, and a plush king bed.

The rest of the hotel was equally amazing. For one, it offered a free transfer service to the airport, so we didn’t have any hassles. Besides that, they had free Wi-Fi, so we could stay connected, free local calls, and even free newspapers. They even had a fitness center for those who wanted to work out on vacation. And even though they don’t have an onsite restaurant, they even serve a great breakfast every morning.

Sybaris Frankfort

4

Most romantic. Imagine finding an adults-only hotel that has pool suites in Chicago! We’re talking about Sybaris Frankfort, where every day is Valentine’s Day, for they have what they call pool suites. In fact, it’s the only hotel with swimming pool in room, Chicago, IL. This adults-only retreat was made for romance, and it’s evident in its choice of stays.

Firstly, the entire concept of Sybaris was to have whirlpool rooms, so all their rooms have huge whirlpools for two right in the room. However, they expanded the concept and introduced pools in the suite rooms, where there’s a legit plunge pool for two through glass doors in the bedroom. Does it get any more romantic than this? We think not! But that’s not all. Our room even had a fireplace that only added to the romantic atmosphere. That’s why it’s one of the best hotels with a jacuzzi in the room in Illinois.

“Staying at Sybaris with a pool in our very room was the ultimate experience!”

WOW Travel

Besides the pool and whirlpool, the rooms also had free Wi-Fi and tea/coffeemakers in all rooms. Overall, there’s a concierge who can arrange for anything that we want and a rental car service right at the hotel.

Harvey House Bed & Breakfast

3

Tucked in Chicago’s wonderful Oak Park neighborhood, Harvey House Bed & Breakfast is one of the most wonderful B&Bs we’ve come across. Most of the rooms come with huge spa baths for two right in the room. So, after a long day of exploring Chicago, there was nothing better than slipping into a bath with your beloved with a glass of wine in hand. The bespoke bath products and fluffy bathrobes only made the experience all the better. Besides the spa baths, the spacious rooms and suites also come with flat-screen cable TVs for watching movies snuggled up together and fireplaces for cold Chicago nights.

Every day at this Illinois B&B began with a hot breakfast that included delights like French toast, oven pancakes, and local delights. The common lounge with the fireplace was a great place to relax on the property, especially before we retired to the rooms. Thanks to the free Wi-Fi, we could plan our itinerary in the days ahead. Finally, since we had our own rental car, the free onsite parking was a blessing.

Sybaris Downers Grove

2

We have yet another Sybaris property on this list; this time, it’s the Sybaris Downers Grove. Did you know that the International Hospitality Rating Bureau voted it as the “Best romantic getaway in the United States?” It’s not surprising, considering that its top rooms are pool suites – plural, yes!

These romantic aquatic oases feature a gorgeous and romantic bedroom with a private heated swimming pool just steps away from the bed! Not only that, but they also have a tropical waterfall, transporting us to world-class places like Bora Bora. The cozy fireplace and the relaxing massage chair in the bedroom only make it all the more romantic. Did we tell you about the misting steam room and attached hot tub? Sigh.

While two of the pool suites are single-level suites, the majestic Chalet suite, which you see above on the right, is a two-storied pool suite!

The Champagne Lodge & Luxury Suites

1

We wanted to stay away from the bustle of Chicago’s downtown and still be as close as we could get to enjoy the attractions and views. That’s why we love the Champagne Lodge & Luxury Suites, which lie less than 20 mi (32 km) from downtown Chicago. Tucked in the quiet residential neighborhood of Willowbrook, this gorgeous hotel made for a secluded romantic getaway while still being close to downtown.

We loved the hotel mostly due to its amazing in-room jacuzzi suites. These spacious suites not only have two-person jacuzzi tubs, but they have them right in the very room. What’s more, these suites also have fireplaces, plush beds, and luxurious bathrooms with all the bespoke amenities and mod-cons we could think of. However, the apex of these luxury spa suites is the pool suite, which has a real swimming pool through a pair of glass doors right in the room! All in all, they offered us all the privacy and seclusion while pampering us with all of the contemporary conveniences possible.

Even though the focus here is the suites, the hotel offers free parking. free Wi-Fi, tea/coffee in the common area, and gorgeous gardens surrounding the property.

Our Verdict!

While we loved all the hotels with pools in the room, Chicago, here are the best ones:

• Best value for money: Best Western Plus O’Hare International South
• Most romantic: Sybaris Frankfort
• Best B&B: Villa D’ Citta

Where to Stay in Chicago

Chicago is home to some of the world’s most richly diverse neighborhoods. So, where do we start, and where do we stay? We first begin with the heart of the city, Downtown Chicago, or The Loop, as it’s famously known. Whether you’re visiting the city for the first time or the nth time, the Loop is a fantastic place to stay. That’s because it’s the city’s most vibrant district and is home to some of the top things to see and do in Chicago. Plus, it also has some of the city’s biggest and best architectural landmarks and attractions.

Secondly, there’s Wicker Park, which is famous for its dining and entertainment avenues and its bustling nightlife. So, those who want to enjoy the Windy City after dark are best off living in this neighborhood. Next, there’s one of Chicago’s best neighborhoods in the form of the Magnificent Mile. This is the city’s prime shopping district and lies just across the Chicago River. What’s more, it’s luxurious to the last mile – no pun intended! Finally, we also loved the vibe and places to stay in Lincoln Park, a leafy and lush neighborhood perfect for checking out the local life.

Recommended Restaurants/Bars in Chicago

• Beard & Belly: One of the unsung heroes of the Windy City’s dining scene, this place is where you come for a late-night slice of pie and a boozy drink. Why? Because the legendary Milwaukee bakery, Honeypie, sits right next to the bar at the storefront. Aside from pies, they also have delicious comfy food options like a burger in a casual setting.
• The California Clipper: This circa-1937, post-prohibition bar is all about its long list of old-fashioned cocktails and glowing red lights setting the mood. Sink into the red leather booths flanking the walls and enjoy weekly live music and drinks. Or do what we did and venture to the Clipper’s back room for late-night dancing to DJ sets meant to channel the spirit of the iconic Bucktown place that shut in 2020, Danny’s. 
• Bartoli’s: We can’t talk about Chicago without talking about deep-dish pizza, can we? Bartoli’s is the place to come to, as owner Brian Tondryk hails from an eminent family of pizza experts. Imagine a flaky, light crust and layers of sweet red sauce and mild mozzarella – absolute heaven. What’s more, there are many versions to choose from, but try the special cheese and spinach pizza. The best bit? They also sell pizzas by the slice.

Recommended Activities in Chicago

• Chicago River 1.5-Hour Guided Architecture Cruise: There’s no better way to appreciate and admire Chicagi’s legendary architecture than from what is the best seat in the house, the Chicago River. This 1.5-hour comprehensive tour saw a fun local guide who regaled us with tales of the city as we navigated through it, covering all three branches of the Chicago River.
• Chicago Underground Pedway & Downtown Secrets Walking Tour: There’s something irresistibly spooky and mysterious about downtown Chicago’s underground passageways, known as “The Pedway.” This walking tour took us to Pedway and all its gorgeous interiors, from both below the ground and above it, with lots of secrets being unraveled along the way.