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Best Hotels for the Holidays in the Chicago Loop

Posted  4 years ago  in  Hotels, Loop List

4 MIN READ - The Loop is where Chicago’s holiday traditions are made, and during the most wonderful time of the year, you need an overnight stay to experience it all. Narrowing down your options can be tricky, but we’re here to help. Check out our list of best hotels for the holidays.

Hotel Essex

Stay iconic in the South Loop during the holidays at Hotel Essex. Steps from Grant Park, the 14-story hotel is the only luxury lifestyle hotel in the area and its landmark building, formerly the Essex Inn, has been a distinct part of the Chicago skyline for decades. Rest easy in the midcentury-inspired guest rooms, which feature floor-to-ceiling city views and high-tech touches such as smart fridges and Bluetooth-enabled bathroom mirrors. When you’re ready to shop, sightsee, and explore, you’re a stroll away from the Art Institute of Chicago, Museum Campus, and the Loop commercial and theater district.

Hotel Julian

Located on Michigan Avenue and a few steps away from Millennium Park and State Street shopping, Hotel Julian provides convenient accommodations for holiday shoppers.

St. Jane

Elf on the Shelf makes his way from the North Pole to Michigan Avenue this holiday season. Don’t let the tradition stop when traveling; the St. Jane elves will make sure to keep Santa in the loop on your child’s good deeds when they are away from home. This Elf on the Avenue package includes overnight valet parking for one car (valued at $68), an Elf on the Shelf for your family to use during your stay (hidden in your room upon arrival), and children under 12 eat free at Free Rein. This package is available for booking dates November 15, 2019-January 3, 2020 and is eligible for St. Jane Junior Suite, Double, or City View Double room types.

Staypineapple Chicago

Boasting an address in the Loop, Staypineapple Chicago is the perfect destination for fun this holiday season. Macy’s is right across the street while the rest of downtown’s top shops are just steps away. To boot, the Chicago Theatre is within a snowball’s throw, and holiday specialties like the Christkindlmarket will be popping up in the neighborhood.

When the day’s fun is over, you’ll be sleeping in style with Staypineapple’s signature Naked Experience featuring European style double duvets along with other thoughtful amenities like Afternoon Delights and cozy bathrobes.

And when you’re hungry after all that shopping or in need of a warm-up, Chicago favorite Atwood Restaurant will be there for you with a belly-filling meal and a hot toddy or your favorite cocktail.

Hotel EMC2

Take your travel experience to the next level at Hotel EMC2, Autograph Collection, located near the Theatre District, Navy Pier, and a variety of shops and restaurants. Inside our hotel, experience upscale amenities and unparalleled services, including friendly greetings from robot attendants, Leo and Cleo, and assistance from Amazon Alexa. Retreat to our chic rooms featuring contemporary décor, and savor creative dining at the Albert, our restaurant specializing in globally inspired cuisine and drinks.

Hostelling International Chicago

Hostelling International Chicago’s friendly staff and festive decor will help to get you in the holiday spirit. The hostel is within walking distance of great landmarks including Millennium and Maggie Daley parks, where you can ice skate the Skating Ribbon and see the snow covered “Cloud Gate” (affectionately nicknamed “The Bean”). With activities every day, you will be sure to experience the best of the holidays in Chicago. Enjoy winter in the Loop with weekly tours of the Christkindlmarket, or stay cozy indoors with movie nights and a weekly hostel welcome party. Staying on Thanksgiving or Christmas? Enjoy a traditional holiday meal with your new hostel family.

Getting around

CTA Holiday Train and Bus

The Allstate CTA Holiday Train is a holiday tradition unique to Chicago, which, due to popular demand, is now accompanied by the Elves’ Workshop Train. Two trains provide twice the amount of fun and festivities to make your holiday extra special.

Just as dazzling and decked out as the Holiday Train, the Elves’ Workshop Train is a six-car train of magic and memories, just like its popular counterpart. It follows the Holiday Train on Saturdays, which are the busiest days, to help ensure everyone has an opportunity to experience this one-of-kind, tradition.

Complementing these two festive trains is the Allstate CTA Holiday Bus, which brings the same holiday spirit and joy to bus riders as it travels throughout Chicago’s neighborhoods.

Millennium Garages

Whether you're exploring State Street, touring the Art Institute of Chicago, or skating at Maggie Daley Park's Skating Ribbon, Millennium Garages has your parking needs covered. Take advantage of daily and multi-day parking rates for your next day trip or extended stay in the Loop. Four underground garages have over 9,000 spaces and are primely located along Michigan Avenue and Columbus Drive with 24/7 access. Book your convenient, discounted parking today.


InterPark now offers its own app, iParkit, which allows you to reserve parking in advance online. With 20 locations in downtown Chicago, iParkit serves every single downtown parking need. Whether you're seeing a live show, strolling along the Riverwalk, or shopping along State Street, you can save time and money by reserving a parking space through iParkit. A reservation guarantees a space and provides full in and out privileges. Scan in and out with your phone or printed receipt, and you're good to go.

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