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Top Resorts in Chicago, Illinois

Delicious food, exciting activities, and an unforgettable getaway await you and the whole family when you book a great deal on Chicago resorts.

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Resort + flight Resort only Flight Only
1 Room, 2 Adults
1 Room, 2 Adults
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Search 128 Resorts in Chicago

At AppleVacations.com, we’ve have 128 different resorts in Chicago for you to explore. Make sure to use the filters to find the perfect Chicago resort for you! Plus, check back often, as we regularly create custom Chicago vacation package deals where you can bundle your flight & hotel for a better deal!
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Level Chicago River North Chicago
Level Chicago River North
Chicago
OUR LUXURY SUITES INCLUDE SPACIOUS AND RIGOROUSLY CLEANED LOUNGE-WORTHY LIVING AREAS FULL EQUIPPED KITCHENS IN-SUITE WASHER/DRYER AND A PRIVATE BALCONY OR PATIO. 24-HOUR GYM POOL DECK WITH JACUZZI AND...
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The St Regis Chicago Chicago
The St Regis Chicago
Chicago
An innovative, architectural marvel crystallized in timeless tradition. Situated at a premier location where the Chicago River meets Lake Michigan, The St. Regis Chicagos impeccably appointed guest ro...
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Hampton Inn Chicago North-Loyola Station Chicago
Hampton Inn Chicago North-Loyola Station
Chicago
Stay minutes from Loyola University at the Hampton Inn Chicago-North Loyola Station hotel. With a convenient location and clean, spacious rooms, our hotel makes the perfect home base for your trip to ...
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The LaSalle Chicago Autograph Collection Chicago
The LaSalle Chicago Autograph Collection
Chicago
A new level of elegance, The LaSalle Chicago provides travelers a stately retreat with twice daily housekeeping service, room service, tailored culinary experiences, and spacious rooms averaging 400 s...
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Hyatt House Chicago-Medical/Uni District Chicago
Hyatt House Chicago-Medical/Uni District
Chicago
The ideal balance of work and play is what you will find at our Medical District/UIC hotel located in Chicago's West Loop. In the heart Medical District, down the street from the University of Illinoi...
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Hyatt Place Chicago- Medical/University District Chicago
Hyatt Place Chicago- Medical/University District
Chicago
The ideal balance of work and play is what you will find at our Medical District/UIC hotel located in Chicago's West Loop. In the heart Medical District, down the street from the University of Illinoi...
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Pendry Chicago Chicago
Pendry Chicago
Chicago
Pendry Chicago has an enviable location inside Chicagos Loop. The Loop is a vibrant area featuring eclectic eateries - shops - theaters and parks. Comprised mostly of high rises - it is also home to t...
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Aloft Chicago Mag Mile Chicago
Aloft Chicago Mag Mile
Chicago
Celebrate your style at Aloft Chicago Mag Mile, a hip new hotel near Michigan Avenues high-end department stores, specialty retail boutiques, and distinguished restaurants. We offer easy-breezy access...
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voco CHICAGO DOWNTOWN Chicago
voco CHICAGO DOWNTOWN
Chicago
Nestled in River North, our downtown Chicago hotel is an oasis of style. voco™ Chicago Downtown features sleek guestrooms with iconic views of the Windy City. The hotel offers walking access to the MA...
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Hyatt Place Chicago Midway Airport Chicago
Hyatt Place Chicago Midway Airport
Chicago
Midway Hotel Centers newest property is composed of 6 floors, including 148 guest rooms and over 2,000 square feet of meeting space. Located just 1 mile south of Chicago International Airport, Hyatt o...
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Map of Resorts in Chicago

Our Favorite Family Resorts in Chicago

Here at Apple Vacations, we know a thing or two about family travel. So we’ve gone through our entire to find our absolute favorite resort and flight deals, along with the dining, entertainment, and other offerings.

All About Our Chicago Resorts

Easy, affordable, and exciting. That’s what it’s like booking a Chicago resort with Apple Vacations. The guesswork is gone when you can compare resort prices, flight + resort rates, perks, and ratings from past guests of the 125 Chicago resorts currently available online.

Chicago is a great vacation destination for families, couples, and anyone looking to have a fabulous time away from their daily routine. Be sure to check out the activities and attractions at your resort and in the surrounding area to make it the vacation of a lifetime.

When you book your Chicago resort with Apple Vacations you just have one job: Find the type of Chicago resort you want, with the best rate, and the extras you’re looking for. That’s it! There are lots of perks and extras at these Chicago resorts, too, like exercise gym, restaurant and room service. Be sure to also check out our top-rated Chicago resorts and our absolute top Chicago resort deals below while you’re at it!

It's All About the Resort Amenities in Chicago

Out of the 125 Chicago resorts currently available on Apple Vacations, there are 50 resorts with Exercise gym, 49 resorts with Restaurant, 31 resorts with Room service and 25 resorts with Cocktail lounge. We have gathered our most popular perks and offerings from our resorts in Chicago and chosen some of our favorite resorts offering those amenities. Check out the nightly prices and guest ratings at Chicago resorts that have your favorite perks and features available.

Amazing Chicago Resorts for Every Type of Vacation

Apple Vacations has a hotel or resort for every kind of trip to United States. Be it a vacation focused on family fun with the kids, a romantic getaway with the special someone, a luxurious resort experience, or an all-inclusive resort vacation where everything is taken care of for you. We currently have 3 luxury, 1 romantic and 1 family-friendly resorts available in Chicago. Here is how our different types of Chicago resorts break down:
  • are great for kids and have an average rating of 3-stars.
  • bring an unsurpassed level of service and quality. They have an average rating of 4-stars.
  • are designed for couples looking to spend some alone time together. They have an average rating of 3-stars.
As with all resorts on Apple Vacations, you can compare nightly rates and flight packages and see the benefits and extras each resort offers before booking. Click on your preferred resort type below.

What kinds of Chicago resorts does Apple Vacations offer?

Chicago has a resort to fit every kind of Apple Vacations traveler. Currently there are dining, romance and family-friendly hotels available.

What kind of amenities are available at Chicago resorts?

Chicago resorts have the following amenities and perks to offer:

  • Exercise gym
  • Restaurant
  • Room service
  • Cocktail lounge
  • Spa

How many hotels and resorts are available in Chicago?

There are 125 different resorts available in Chicago right now on Apple Vacations. Book a beautiful resort near popular points of interest in Chicago today!

Hotel And Resort Destinations Like Chicago

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Popular Resort Destinations in United States

While reasonable effort has been made to ensure the accuracy of the information on this website, Apple Vacations does not assume responsibility for any errors or omissions.
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