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Chicago Hotels & Vacation Rentals for Christmas

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Enjoying All the Best of Chicago with Vacation Rentals for Christmas

With an iconic skyline, plenty of famous attractions and great places to eat and drink it's easy to see why Chicago is such a popular holiday destination. It's one of the very best cities for picking up all your gifts or treating yourself to the best brands on The Magnificent Mile. Come and tick everything off your list or stay for the big day.

Christmas in Chicago: Top Accommodations

House Near West Side
Dec 19 - Dec 26
$234 per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation Home in Near West Side with Grill

5.0
Outstanding (2 ratings)
Near West Side, Chicago, Illinois, United States
Free cancellation
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Apartment The Gap
Dec 21 - Dec 28
$153 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Lovely Rental Apartment in The Gap

4.0
Very good (1 rating)
The Gap, Chicago, Illinois, United States
Free cancellation
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Apartment Near North
Dec 19 - Dec 26
$133 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Near North with On-Site Parking, Near John Hancock Center

Near North, Chicago, Illinois, United States
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Where to Dine for Christmas in Chicago

Where to Dine for Christmas in Chicago

Between all the shopping and sightseeing, you can look forward to top dining options during your stay over the holidays. From haute cuisine to pizza parlors serving Chicago's best-loved treats, there's something to suit every taste in the Windy City. Try the foods that make the city famous when you book Chicago hotels for Christmas.

  • 1. Chicago Pizza and Oven Grinder Company

    The city is famous for its particular style of pizza - a satisfying deep-dish pie, often with stuffed crusts and plenty of fresh ingredients to fill up even the hungriest traveler. This is one of Chicago's most popular parlors, a cozy spot to warm up in December.

  • 2. Alinea

    One of the city's very best fine dining establishments, with New American-style food. Alinea describes itself as 'not a restaurant, at least in the conventional sense'. Indeed, its three Michelin stars have made it one of the world's premier restaurants, where you book 'experiences' rather than meals as such. This is superb for an unforgettable pre-Christmas treat, especially as a couple.

  • 3. Piccolo Sogno

    Chicago is known for its Italian food, which goes well beyond just pizza. In this rustic and charming restaurant,you can savor a traditional and refined ambience and choose from a huge wine list. Piccolo Sogno is in the elegant River West neighborhood and is particularly great for families looking to re-energize after a day of shopping and sightseeing.

Best Places to Stay for Christmas in Chicago

House Calumet Heights
Dec 21 - Dec 28
$276 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Calumet Heights with Yard

Calumet Heights, Chicago, Illinois, United States
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Apartment Near North
Dec 21 - Dec 28
$172 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Near North with On-Site Parking, Close to John Hancock Center

Near North, Chicago, Illinois, United States
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House Chatham
Dec 21 - Dec 28
$199 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Chatham

Chatham, Chicago, Illinois, United States
Free cancellation
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Best Holiday Attractions in Chicago

Best Holiday Attractions in Chicago

Chicago vacation rentals offer a magical experience during the holidays. Bringing the best of old European tradition and a multitude of shopping opportunities, Chicago always hits the spot at Christmas. You will see how the city celebrates, with festive markets, inspirational window displays and shows to get you in the mood.

  • 1. Holidays at Macy's on State Street

    When you think of Christmas shopping in Chicago, this is probably one of the first places that comes to mind. Even just window shopping and admiring the attractive displays is always enjoyable. Of course, you can head inside too and check out multiple floors housing every kind of gift.

  • 2. Christkindlmarket

    This German-style extravaganza is traditional Christmas at its very best. Grab a mug of warm mulled wine and munch on Bratwurst as you browse crafts, clothing and much more. It's inspired by the 16th century Nuremberg market in Germany and brings the best of old-world charm to ultra-modern Chicago.

  • 3. The Nutcracker at Joffrey Ballet

    This wonderful, Christmas-themed ballet show has become a yearly tradition for many and it's easy to understand why. The Joffrey Ballet is very close to Millennium Park in downtown, and as a world-class venue you'll appreciate one of the very best performances of The Nutcracker you could hope to see.

Recommended Accommodations for Christmas in Chicago

Apartment Near North
Dec 21 - Dec 28
$245 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Family Friendly Apartment in Near North with On-Site Parking, Near John Hancock Center

Near North, Chicago, Illinois, United States
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Apartment West Town
Dec 19 - Dec 26
$130 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Beautiful Rental Apartment in West Town with Large Balcony + City Views

5.0
Outstanding (2 ratings)
West Town, Chicago, Illinois, United States
Free cancellation
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Apartment South Austin
Dec 21 - Dec 28
$200 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in South Austin with Yard

5.0
Outstanding (1 rating)
South Austin, Chicago, Illinois, United States
Free cancellation
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Things to Do With Your Family During Christmas Vacation in Chicago

Things to Do With Your Family During Christmas Vacation in Chicago

Finding hotels for Christmas in Chicago is ideal for making the most of the holidays with the family. There's plenty to do in this enormous city for people of all ages. You can go ice skating and get lost in a winter wonderland that will keep you and the kids happy for many hours throughout December.

  • 1. Glenview Ice Center

    This is particularly great for families, offering a large indoor area for ice skating or evening events including roller discos for adults who want to party winter-style. Millennium Park is an excellent outdoor alternative and great for admiring the lights and skyscrapers as you skate.

  • 2. Wonderland Express at Chicago Botanic Garden

    These glorious gardens are a must-see at any time of year. At Christmas in particular, be sure to catch the model trains which pass by a miniature version of Chicago's most iconic landmarks. Ice sculpting and free movie events throughout the holidays offer even more reasons to visit.

  • 3. Winter WonderFest at Navy Pier

    There's a lot to please all ages at this winter bonanza of events. Ride a toboggan, try your hand at mini golf, and have fun with more great ice skating opportunities. There are plenty of mixed stalls to buy food from and you are also allowed to bring your own. There is also an IMAX cinema for catching the current holiday releases on the (very!) big screen.

Top Offers for Christmas in Chicago

Apartment Near North
Dec 21 - Dec 28
$245 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment in Near North with On-Site Parking, Near John Hancock Center

Near North, Chicago, Illinois, United States
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Apartment Near North
Dec 19 - Dec 26
$143 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Near North with On-Site Parking, Near John Hancock Center

Near North, Chicago, Illinois, United States
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Apartment Grand Boulevard
Dec 21 - Dec 28
$172 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Rental Apartment in Grand Boulevard

3.0
(2 ratings)
Grand Boulevard, Chicago, Illinois, United States
Free cancellation
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Information about Chicago Hotels & Vacation Rentals for Christmas

📏 Average home size 86 m²
🥳 Busiest month April
🛏️ Popular home types House rental and Apartment rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months 17 °F in January and February
🌧️ Rainiest months March and April

Frequently Asked Questions

Chicago Hotels & Vacation Rentals for Christmas: What is the nightly price for a stay?

On average, you can get a great vacation home for somewhere between $197 and $542 and find discounts up to 36%!

Chicago Hotels & Vacation Rentals for Christmas: is there a good selection of vacation homes for groups of guests?

Apartment rental in Chicago fits 4 people.

Chicago Hotels & Vacation Rentals for Christmas: what types of vacation homes can I find?

We would advise choosing from our incredible selection of House rentals and Apartment rentals in Chicago.

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Average Nightly Rental Prices in Chicago

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Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental availability information in Chicago

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