Chicago Adults Only Vacation Packages

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Experience the vibrant nightlife and cultural attractions of Chicago

Chicago is renowned for its iconic skyline filled with towering skyscrapers, offering a stunning urban landscape. Visitors can immerse themselves in the vibrant theater scene, marvel at the architectural wonders, and explore world-class museums that showcase art and history. The city is dotted with impressive monuments that pay homage to its rich heritage. Entertainment options abound, from live music performances to comedy clubs. Additionally, the surrounding area boasts picturesque scenery, perfect for leisurely strolls or bike rides. And for those seeking retail therapy, Chicago offers exceptional shopping experiences with a blend of high-end boutiques and bustling markets.

4 Night Adults Only vacations in Chicago

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Top reasons for your vacation to Chicago

  • Iconic Skyline: Marvel at Chicago's towering skyscrapers and stunning urban landscape.
  • Vibrant Theater Scene: Immerse yourself in the lively theater scene and catch world-class performances.
  • World-Class Museums: Explore top-notch museums showcasing art and history.
  • Impressive Monuments: Admire the city's rich heritage through its impressive monuments.
  • Breathtaking Scenery: Enjoy leisurely strolls along Lake Michigan and take in the picturesque surroundings.

Book a Package and Save Money on Your Chicago Vacation

A travel package combines flights with hotels or car rental, making it convenient to book everything in one place. It saves time and effort by eliminating the need to search for separate deals. Additionally, booking a package can help save money and offers the flexibility to customize your vacation based on your preferences and budget.

Looking for a fun-filled adults-only vacation? Look no further than Chicago! With its stunning skyscrapers, world-class theater, impressive architecture, renowned museums, vibrant art scene, iconic monuments, exciting entertainment options, breathtaking scenery, and fantastic shopping, booking a package in Chicago is the perfect idea for your adults-only vacation.

How to Save Money on a Vacation to Chicago

  • Take advantage of Expedia's OneKey program to collect points and save money on your bookings.
  • Consider using public transportation such as the Chicago Transit Authority (CTA) buses and trains to save on transportation costs.
  • Look for discounted or free activities and attractions such as free museum days, walking tours, and outdoor concerts.
  • Save money on dining by exploring local food markets, food trucks, and affordable eateries instead of expensive restaurants.
  • Book your accommodations in advance and consider staying in budget-friendly neighborhoods or opting for Airbnb or vacation rentals instead of hotels.
  • Take advantage of Chicago's bike-sharing program, Divvy, for a cost-effective and fun way to explore the city.
  • Check for discounted theater tickets, comedy shows, and live performances on websites like Goldstar or TodayTix.
  • Visit the Chicago CityPASS website for discounted admission to popular attractions like the Shedd Aquarium, Skydeck Chicago, and the Art Institute of Chicago.
  • Take advantage of free events and festivals happening in Chicago throughout the year, such as the Taste of Chicago or the Chicago Jazz Festival.
  • Consider purchasing a Chicago Go Card or CityPASS for bundled savings on attractions, tours, and experiences.

Where to Stay in Chicago

Chicago offers a diverse range of neighborhoods for adults-only travelers. From the vibrant nightlife and trendy restaurants in River North, to the artsy vibe and vintage shops in Wicker Park, there's something for everyone. Explore the historic architecture in the Loop or enjoy the waterfront views in Streeterville.

  • Downtown Chicago: Experience the grandeur of skyscrapers, immerse in urban culture, explore world-class architecture and museums, cruise along the scenic river, indulge in theater and art, and enjoy vibrant entertainment. Downtown Chicago offers a unique atmosphere that is perfect for adults seeking a mix of history, culture, and entertainment.
  • Lincoln Park: Discover the charm of a zoo in an urban setting, enjoy picturesque lake views, admire towering skyscrapers, relish in scenic beauty, dine at exquisite restaurants, shop to your heart's content, and embrace nature with birdwatching. Lincoln Park provides a diverse and lively atmosphere for an adults-only vacation.
  • Near North Side: With its majestic skyscrapers, urban allure, architectural wonders, picturesque scenery, world-class museums, meandering river, vibrant art scene, upscale shopping, serene lakefront, and exquisite dining options, Near North Side offers a perfect adults-only vacation experience in the heart of Chicago.

Explore the best places to visit in Chicago

Chicago (and vicinity) is an ideal destination for an adults-only vacation vacation. Immerse yourself in the vibrant urban atmosphere, surrounded by towering skyscrapers and stunning architecture. Indulge in the city's renowned theater scene, visit world-class museums and art galleries, and admire iconic monuments. Experience thrilling entertainment options and breathtaking scenery along Lake Michigan. Shop to your heart's content in the city's trendy boutiques and department stores. Chicago offers a perfect blend of culture, excitement, and relaxation for adult travelers.

  • Rivers Casino: This bustling casino offers a unique blend of entertainment options. Try your luck at the gaming tables or enjoy a thrilling hockey match. Indulge in delicious dining options and sip on handcrafted cocktails at the bar. Experience live music performances and catch a show at the theater. For a fun twist, go bowling and immerse yourself in the lively atmosphere.
  • Aragon Ballroom: This iconic music venue showcases the best of Chicago's music scene. Dance the night away to urban beats and enjoy the energetic atmosphere. Admire the stunning skyscrapers and take in the breathtaking views of Lake Michigan. Immerse yourself in the architecture and art that surrounds you. The friendly people and scenic backdrop make this a must-visit spot for music lovers.
  • Civic Opera House: Immerse yourself in the grandeur of opera at this historic venue. Marvel at the impressive skyscrapers and architectural beauty. Explore the surrounding museums and monuments for a cultural experience. Admire the scenic river views as you indulge in world-class performances. The combination of art, theater, and entertainment makes this a unique attraction in Chicago.

Best months to visit Chicago

Chicago boasts a year-around average temperature of 51.3°F, peaking at 75.9°F in July, its warmest month, and dipping to an average low of 24.8°F in January, the coolest. Rainfall averages at 82.8mm annually, with May seeing the heaviest showers and February being the driest month.


Monthcalendar iconTemperature (Fahrenheit)temperature iconRainfall (mm)rain icon
January24.852.3
February28.849.3
March38.869.1
April50.592.5
May61.0104.9
June71.1103.1
July75.9101.9
August74.1101.3
September66.484.1
October54.382.3
November41.586.9
December28.965.3

Find amazing adults only vacations in Chicago

Why choose an adults-only resort for my vacation in Chicago?

Book adults-only accommodation for your Chicago getaway to enjoy privacy and tranquility. With no little ones running around, the atmosphere at an adults-only resort tends to be more sophisticated. These types of resorts are especially popular among couples. The intimacy of adults-only hotels is ideal for a romantic escape and honeymoons. On Expedia, you'll encounter a vast array of affordable adults-only vacations to Chicago.


What amenities are typically included in adults-only resort packages for Chicago?

As they're geared toward relaxation, adults-only vacation packages to Chicago usually include resorts with amenities like swimming pools, spas, and on-site restaurants. If you book an all-inclusive vacation package to Chicago, you'll have all meals and drinks included, too. All-inclusive adults-only resorts typically offer a tempting mix of local cuisine and international favorites. When searching for packages, you can take advantage of the filters to pin down adults-only resorts you desire.


Are there any age restrictions for staying at adults-only resorts in Chicago?

Typically, you'll need to be over the age of 18 to go on an adults-only vacation to Chicago. Each resort has its own policy, though. Some consider 16 and 17-year-olds to be adults, while others even accept those over 13 years of age. In other cases, you may need to be over 21. Given that there are lots of differences, it's a good idea to double-check before booking. Luckily, Expedia makes this information clear so there are no surprises.


Can I expect a more romantic atmosphere at adults-only resorts in Chicago compared to other accommodations?

Yes, if you're seeking a romantic adults-only Chicago vacation, you'll enjoy more intimate vibes in adult-only resorts. That's because they include amenities that are ideal for couples. The look and feel is often more sophisticated too, and you'll find amenities are usually spread out to create a feeling of privacy. You may also enjoy a more personalized service, with concierge and masseurs on hand. Take your pick from Expedia's plethora of romantic adults-only resorts in Chicago.


Are there any special events or activities tailored for adults at adults-only resorts in Chicago?

When you stay at an adults-only resort on your Chicago vacation, you can expect romantic activities like candle-lit dinners under the stars. Adult-only hotels typically offer fine dining, with talented chefs preparing exquisite meals. Adults-only resorts in Chicago often boast indulgent spas, too. Here, you can pamper yourself with rejuvenating treatments and unwind with relaxing massages. Before booking your Chicago vacation package on Expedia, you'll be able to view what each property offers.


How to find last-minute deals for adults-only packages on Expedia?

Wizz over to Expedia's last-minute deals page to view some of the best last-minute deals for an affordable Chicago vacation from $917. Remember, you're more likely to land a last-minute saving during the low season when fewer people travel. It's also a good idea to be flexible with your dates. That's because prices can vary by day. Luckily, Expedia's easy-to-use search wizard and nifty filters make booking a last-minute escape quick and easy.


Can I cancel my adults-only vacation booking easily?

Yes, as many of Expedia's adult-only vacation packages to Chicago are flexible, you can often cancel for free. Simply log in to your account and head to the “Trips” section and follow the steps. Not all packages are flexible, however, so you should read the cancellation policy before booking your 2024 trip. The good news is you'll see this displayed on Expedia before you reach the booking page. The free cancellation search filter is handy, too.


Why book my adults-only vacation with Expedia?

Thanks to exclusive offers, you'll get some of the best-priced deals for adults-only Chicago vacations when booking with Expedia. With a wide selection of flights and hotels, you'll easily find the right trip for you. The One Key reward program lets you earn points on select stays that you can then cash in to save on future trips, on top of exclusive member-only discounts. Best of all, joining One Key is free. On top of these benefits, the 24/7 support and booking protection gives you peace of mind when booking with Expedia.

Top Adults Only Chicago Hotels

Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown
Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown
Lake Forest
  • 7 min drive from Naval Base Great Lakes
Stay at this vacation home in Lake Forest. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Forest Park ...
9.8/10 Exceptional! (100 reviews)
Easy stay!
"I rented this house for my family who was in town for a wedding. The pictures don’t do it justice, it’s updated, clean, and very spacious. Would definitely rent again!"

Reviewed on Sep 18, 2024

Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown
Holiday Inn Express & Suites Chicago Matteson, an IHG Hotel
Holiday Inn Express & Suites Chicago Matteson, an IHG Hotel
2.5 out of 5
950 Lake Superior Dr, Matteson, IL
  • 2 hours drive from Naval Base Great Lakes
Book a stay at this business-friendly hotel in Matteson. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hollywood Casino Amphitheatre ...
6.4/10 (811 reviews)
"First this hotel needs to update there website, they do not offer a Continental breakfast not even coffee in the lounge. When we called prior to booking and were told they did and found out the opposite, this was a bit irritating. The room we were given looked like the bed was half made. There were ..."

Reviewed on Sep 17, 2021

Holiday Inn Express & Suites Chicago Matteson, an IHG Hotel
The Champagne Lodge & Luxury Suites
The Champagne Lodge & Luxury Suites
3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
  • 2 hours drive from Naval Base Great Lakes
Stay at this 3.5-star boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,008 reviews)
"Had a great stay with great service. Will be back"

Reviewed on Sep 23, 2024

The Champagne Lodge & Luxury Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.