Get into the holiday spirit at these must-visit Chicago restaurants

by The OpenTable team

Updated December 10, 2021

The holidays are all about good food and good friends. So Stella Artois and OpenTable are bringing them together with an exclusive Holiday Guide featuring some of the best restaurants Chicago has to offer. Savor the season with Stella and the ones who matter most by booking your festive get-together today.

Elephant & Castle - Chicago Wabash Ave.

4.5

4.5 (772)

$30 and under

American

Lakeshore East

About the restaurant

Nestled on the corner of Wabash and Lake, Elephant & Castle is your go-to British pub in the heart of Chicago's vibrant theatre and shopping districts. Just steps from the iconic Chicago Theatre and two blocks from the scenic Chicago Riverwalk, we offer classic British pub fare like fish and chips, hearty breakfasts, and live sports on big screens. Whether you're stopping by for happy hour, catching a football match, or grabbing a bite before a show, Elephant & Castle delivers an unforgettable pub experience right in downtown Chicago.

Top review

Ross

Dined 3 days ago

Great atmosphere with that British vibe. Pot pies were delicious. And server Malique was outstanding with friendly, courteous, and knowledgeable service… and great sense of humor too!

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Popular dish

Fish & Chips

Popular dish

Highland Bread Pudding

Popular dish

Steak & Mushroom Pie

Elephant & Castle - Chicago Adams St.

4.7

4.7 (367)

$30 and under

American

Downtown / Loop

About the restaurant

Located in Chicago's bustling central business district, Elephant & Castle on Adams offers an authentic British pub experience with hearty pub fare like fish and chips, classic breakfasts, and live sports. Whether you're grabbing a bite after visiting the Art Institute, catching football matches after work, or enjoying happy hour near Willis Tower, we've got you covered. Conveniently attached to the Club Quarters Central Loop hotel, Elephant & Castle is your go-to sports pub for great food, drinks, and a lively atmosphere in the heart of Chicago.

Top review

Laura

Dined 4 days ago

Portion size is reasonable for the price and good quality. Helpful servers. I'll be back

Bar Siena - West Loop

4.5

4.5 (3287)

$30 and under

Italian

West Loop

About the restaurant

Perfectly Centralized In Chicago's West Loop 'Restaurant Row', The Two-Story, 8,000-Square-Foot Restaurant Is The Sibling Of DineAmic Hospitality'S River North Staple Eatery, Siena Tavern. Bar Siena Offers Diners The Perfect & Approachable Setting To Enjoy Lunch, Dinner, Late Night, And Weekend Brunch. The Menu Features An Expansive Italian Street Food And Pizza Bar Selection, All Served Within The Streets Of Fulton Market. Our Team Of Hospitality Professionals Are Thrilled And Dedicated To Host Your Next Dining Experience, Private Event Or Catering Function!

Top review

Steve

Dined 2 days ago

Food quality and service were both outstanding. Highly recommend for business lunch.

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Harry Caray's Tavern - Navy Pier

4.2

4.2 (957)

$30 and under

American

Gold Coast / Streeterville

About the restaurant

Located near Navy Pier’s main entrance, Harry Caray’s Tavern combines a waterfront setting, family-friendly American and Italian comfort food, and an extensive collection of sports and pop culture memorabilia for a truly unique dining experience. The mahogany-paneled walls and display cabinets showcase a rotating collection of treasures, including artifacts, photos, and vintage newspapers celebrating Chicago sports legends and cultural icons.

Guests can enjoy the patio's stunning views of Lake Michigan and Navy Pier’s vibrant atmosphere. In winter, the outdoor dining igloos, lakefront curling, and the cozy Lakefront Lodge offer seasonal charm.

With HDTVs throughout the restaurant and bar, Harry’s is the perfect spot to catch major sporting events. The restaurant is also proud to have a variety of celebrity partners, including Patrick Kane, Ryne Sandberg, and Richard Dent, and many other of Chicago’s biggest athletes, Hollywood stars and radio personalities.

Top review

Cynthia

Dined on Jan 4, 2025

Jalapeño burger was really good. So was the meatball sandwich. Service was also good. I'd definitely come back.

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Experience

Groundhog Day Celebration

Pizano's Pizza & Pasta - Madison

4.6

4.6 (336)

$30 and under

Italian

Downtown / Loop

About the restaurant

Pizano’s Pizza & Pasta blends classic Italian recipes and fresh takes on traditional fare in one satisfying menu. The son of Pizzeria Uno founder and deep dish creator Rudy Malnati Sr., Pizano’s owner Rudy Malnati Jr. knows what makes an Italian dish truly delicious; high-quality ingredients, authentic recipes, and excellent service. Bowls of seafood marinara and chicken alfredo share menu space with bubbling deep dish pizza and Pizano’s award-winning thin crust pizza, a favorite of critics and visitors alike, including Oprah Winfrey, who featured the restaurant on her show. Located in the heart of Jeweler’s Row, the Madison Street location embodies historic Chicago dining, as timeless songs by Sinatra and Martin fill the air while diners gaze at numerous photos of famous athletes and entertainers line deep, rich wooden walls.

Top review

Nate

Dined 1 day ago

Noah is the guy, love the food, the history and the vibes!

The Black Barrel Tavern

4.7

4.7 (151)

$30 and under

Contemporary American

West Loop

About the restaurant

We are excited to be bringing our newest concept to a wonderful part of the city, the West Loop! Updated Americana and Brunch fare served in a sport-friendly meeting place with craft beers, signature cocktails, and a kitchen open until midnight. --- We are offering curb side pick up on our meals, family style meals available with the addition of beer, liquor and wine to go for a full at home Black Barrel Tavern experience.

Top review

DonVIP

Dined 3 days ago

Really good wings and cheeseburgers but $40 for a shot of Blantons is ridiculous. C’mon man.

Harry Caray's Italian Steakhouse - Rosemont

4.5

4.5 (2642)

$31 to $50

Steak

Rosemont

About the restaurant

Located just minutes from the O'Hare International Airport Harry Caray's in Rosemont brings the same friendly confines and award-winning Italian Steakhouse cuisine from the legendary downtown location to Chicago's northwest suburbs. The casual to fine dining restaurant specializes in the finest prime, aged steaks, chops and classic Italian cuisine. The friendly, energetic atmosphere embodies the amiable personality of the restaurant's namesake. The dark mahogany, mosaic floor, white-jacketed servers, white tablecloths and a veritable museum of baseball history combine to create a warm and casual elegance.

Top review

PatVIP

Dined 2 days ago

The hostess gave a wonderful welcome and greeting to our birthday guest. Our server Jason was excellent in all regards. Our birthday guest was very impressed with the souvenir happy birthday menu and complimentary dessert. We will be back soon!

Paisans Pizza - Berwyn

4.4

4.4 (166)

$30 and under

Italian

Berwyn

About the restaurant

Paisans is a modern Italian-Americano restaurant, offering home style entrees, burgers, sandwiches and desserts, weekly lunch and dinner specials in our 20,000 square foot industrial style building.

Top review

EllenVIP

Dined 5 days ago

Really like this location. It was interesting that they were playing loud club music for early afternoon. Food always good.

Remington's

4.7

4.7 (3268)

$30 and under

American

Downtown / Loop

About the restaurant

Turn to Remington's to create a memorable experience for your upcoming event! Our venue can accommodate your group of 10 to 225 guests for breakfast, lunch, dinner, or a cocktail reception in a variety of private and semi-private dining spaces. Whether you're having an intimate gathering or a large corporate meeting, our sleek restaurant is the perfect spot to host your VIP guests in the heart of Chicago's Millennium Park area.

Top review

Karen

Dined 4 days ago

Very impressed with the food and service at Remingtons. It was our first time, we went before a show. We had the ribeye and loaded potato and Brussels sprouts plus shrimp appetizers. Everything was fantastic. It’s a lovely atmosphere and service was spot on.

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The Cubby Bear Chicago

3.2

3.2 (11)

$30 and under

American

Wrigleyville

About the restaurant

Established in 1953, The Cubby Bear overlooks Wrigley Field's famous Marquee. Since its opening, it established deep roots in Chicago’s Wrigleyville neighborhood. It has witnessed some of the most historic Cubs victories and live musical performances. Decades later it remains a top destination for year round live music and sports entertainment.

With over 30,000 square feet of space, you can can enjoy live music, watch your favorite sporting event, choose your favorite dish from our menu, or attend a party in one of the private rooms overlooking the Marquee. Grab a seat at one of our many bars or find a table outside on our new patio. We've got a spot for you!

Top review

EduardoH

Dined on Jul 23, 2022

Great place to enjoy the evening. The band was awesome to listen to, well being with friends.

Old Town Pour House

4.6

4.6 (219)

$31 to $50

American

Chicago

About the restaurant

Vibrant bar and restaurant featuring 90 beers on tap (30+ dedicated to local breweries) and modern American food with chef-driven twists.