Are you planning a staycation in Chicago? Beware of our team at Travel Taste Discover! They are always more than willing to contribute to your travel plans.
It’s too late! Everyone is already debating their favorite luxury hotels, B&Bs, and boutique hotels for a Chicago staycation. Not only that, but we are also receiving suggestions for the best activities for staycationers left, right, and center. From a dramatic spa experience at AIRE Ancient Baths and dainty romantic packages at Hotel EMC2 to thrilling experiences in escape rooms, there is so much to be explored in the Windy City.
Why book a stress-inducing flight when you can plan a route in your city to a destination much closer to home than you imagined? Hop into the car, as we have already rounded up the best Chicago staycation ideas.
PS. These Chicago staycation ideas are for everyone, whether you are traveling as a couple, with family, or alone. So, stay with us until the end.
Staycation In Chicago For Couples
Hotels For A Romantic Staycation In Chicago
The Royal Sonesta Chicago River North
Address: 505 N State Street, Chicago, IL 60654, USA
The Royal Sonesta Chicago River North has crept into the hearts and Instagram feeds of many couples due to its luxury spa suites, which make for the most romantic staycation in Chicago. The generous in-room amenities are perfect for couples, especially the jetted spa tub and cozy robes. You can even order noshes and treats to your room with the CBR’s to-go menu.
Villa D’ Citta Bed & Breakfast
Address: 2230 N Halsted Street, Chicago, IL 60614, United States
If you and your partner are always looking for excuses to travel, this is one of the best staycation hotels in Chicago, especially if the idea of an old-world Tuscan-style villa excites you. Villa D’ Citta Bed & Breakfast is a romantic B&B for couples for a stay within their own city. You can book a luxurious Grand Tuscan Suite (with an oversized jacuzzi whirlpool tub) or a private and cozy Caesar’s Lair Suite, which comes with a plush queen bed.
Hotel EMC2, Autograph Collection
Address: 228 E Ontario Street, Chicago, IL 60611, United States
This boutique hotel packs a lot in its Be Mine Package for couples seeking a staycation in Chicago. After all, what’s a better feeling than returning to a luxurious, romantic boutique hotel room where sateen weaves bedding, open-glass showers, and plush bathrooms are waiting to wrap things up? But before that, take advantage of the $25 credit to the chic Italian-inspired Albert restaurant.
Staycation Ideas For Couples In Chicago
AIRE Ancient Baths
Address: 800 W Superior Street, Chicago, IL 60642, United States
Spas are always a good idea for an ideal Chicago staycation, and AIRE Ancient Baths never miss the spot by offering the perfect romantic getaway. Choose the 90-minute Ultimate Couples Bath, which includes thermal baths and aloe vera scrubs reserved just for you and your partner. Or the Escape Together 45’ relaxing massage, which is a must-try thing to do in Chicago’s staycation.
Chicago Electric Boat Company
Address: 300 N State Street Suite EE, Chicago, IL 60654, United States
To explore your own city in a unique way with your romantic partner, book a ride with Chicago Electric Boat Company, one of the best staycation ideas. You can be a captain yourself or comfortably sit back and cruise around the river. Choose a donut boat or a retro boat as they onboard fewer passengers, offering you a secluded time during your staycation in Chicago.
Staycation In Chicago For Families
Family Friendly Hotels For A Staycation In Chicago
Le Méridien Essex Chicago
Address: 800 S Michigan Avenue, Chicago, IL 60605, United States
Le Méridien Essex on Michigan Avenue opens to scenic views of the city and is surrounded by the most popular attractions for your list of things to do in a staycation. Pets are allowed to accompany you and your kids as you indulge in luxurious experiences before heading out to nearby locations like Lincoln Park Zoo, Grant Park, and Adler Planetarium.
Courtyard Chicago Downtown/Magnificent Mile
Address: 165 E Ontario Street, Chicago, IL 60611, United States
If shopping is your idea of a perfect staycation in Chicago, it doesn’t get any better than Courtyard Chicago. With exciting packages like the American Girl Store Package and the nearby premier shopping district on Magnificent Mile, convenience meets you at every corner as you stay in the luxurious rooms, dine in, or take a dip in the indoor pool at this modern hotel.
Kimpton Gray Hotel
Address: 122 W Monroe Street, Chicago, IL 60603, United States
For city folks looking for a sophisticated and stylish retreat, Kimpton Grey Hotel is one of the best staycation hotels in Chicago. There is a lot to be enjoyed by the whole family, including thoughtful boutique amenities like pet-friendly accommodations, custom-designed bikes for a ride around the city, and a children’s book checkout.
Things To Do In Staycation For Families
Fox In A Box Escape Room
Address: 47 W Polk Street, suite l5 basement, Chicago, IL 60605, United States
Thieves, Zodiac killer, prison blocks, and a secret agent – Fox In A Box Escape Room is the best escape room center in Chicago with tons of things to do during your staycation. It’s already a popular hangout spot for families, but you must keep it into your staycation ideas and plans for an overdose of adrenaline-filled, heart-pumping experiences.
Altitude Chicago Trampoline Park
Address: 404 N Armor Street, Chicago, IL 60642, United States
Spread on a 33,000 sq ft facility, this unique trampoline park is a go-to spot for your staycation in Chicago. Perfect for participants of all ages, families, and kids who will enjoy the safe and exciting activities like the spinning wheel of Wipeout and the gravity-defying performance trampolines with a 4 or 6-foot landing zone.
Skydeck Chicago
Address: 233 South Wacker Dr, Chicago, IL 60606, United States
Explore Chicago in all its glory from the 103rd floor, like you’re seeing it for the first time. Many people are intimidated by the dazzling height of this observation deck, but if you have a thing for exceptional vantage points, do take your whole family during your Chicago staycation to this tallest building in the city with views spanning across four states!
Solo Staycation in Chicago
Best Staycation Hotels In Chicago For Solo Travelers
Waldorf Astoria Chicago
Address: 11 E Walton Street, Chicago, IL 60611, United States
Solo guests would love to explore new experiences during their staycation in Chicago, which is why this luxury hotel, situated in a high-rise building, offers the best amenities that fit your Chicago staycation ideas and expectations, such as cocktails in an evening lounge, an indoor heated lap pool, and a modern fitness center.
Moxy Chicago Downtown
Address: 530 N La Salle Drive, Chicago, IL 60654, United States
If you are more interested in unique traveling journeys, then choose this chic downtown hideaway, where boredom is unheard of. Moxy takes pride in its designated playground zone, which includes cozy living rooms, a Game Room, the Moxy Vinyl Library, late-night cocktails at Bar Moxy, and the outdoor Zombie Taco patio, which never lets you run out of staycation ideas.
Viceroy Chicago
Address: 1118 N State Street, Chicago, IL 60610, United States
Looking for a peaceful escape during your Chicago staycation, with lots to do and little to stress about? Then, the best staycation hotels in Chicago for you would be specialty accommodations and boutique hotels, like Viceroy Chicago. In the heart of Gold Coast, this hotel offers posh bedrooms with lake or city views to relax as much as you want during your staycation in Chicago.
Staycation Ideas In Chicago To Do Alone
Take A Stroll Around The City
Chicago is filled with beautiful buildings, lakefront trails, lush parks, delicious culinary spots, and the best museums. Spend the day on your own and take your time intimately exploring these attractions during your staycation in Chicago. Want more ideas? Check out the Cloud Gate sculpture, Field Museum, West Loop’s Fulton Market, Shedd Aquarium, Devon Avenue or the Adler Planetarium.
Treat Yourself To A Solo Date
Get out of your comfort zone and build the best relationship with yourself with a solo date. After all, it’s the perfect staycation idea if you are on your own. Treat yourself to the best sushi of your life at Jinsei Motto, a culinary-driven brunch at Lost Reef, or a hearty S’mores Croissant or Cinnamon Banana Bread at Cafe Robey.
A “Room With A View” in Chicago
The Best Hotels In Chicago With Incredible Views
These hotels in Chicago are a completely luxurious experience, with river views, Lake Michigan views, and skyline, navy pier, and city views.
