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

by The OpenTable team

Updated 10 December 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 (723)

$30 and under

Unspecified

Lakeshore East

About the restaurant

Get your Brit On at Elephant & Castle! Nothing feels as warm and inviting as sitting down at the pub and sampling a taste of Britain. The old Union Jack behind the bar may be faded, but the mood is vibrant. Located on the Corner of Wabash and Lake, just steps from the legendary Chicago Theatre and two blocks from the scenic Chicago Riverwalk in the heart of Chicago's theatre and shopping districts.

Top review

Sally

Dined 5 days ago

Love it!! We will be back!! Would recommend!! Thanks again

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Popular dish

Highland Bread Pudding

Elephant & Castle - Chicago Adams St.

4.3

4.3 (360)

$30 and under

British

Downtown / Loop

About the restaurant

Get your Brit On at Elephant & Castle! Nothing feels as warm and inviting as sitting down at the pub and sampling a taste of Britain. The old Union Jack behind the bar may be faded, but the mood is vibrant. Strategically situated in the heart of Chicago's central business district and attached to Club Quarters Central Loop hotel, E&C Adams is the best of both worlds whether you need convenience to tons of businesses and government buildings or want to see one of the many sights within walking distance such as the Symphony Center, Willis Tower, and the Art Institute of Chicago.

Top review

OpenTable Diner

Dined on 18 Jul 2024

Loved it! The food was amazing and bread pudding was so good!

Bar Siena - West Loop

4.5

4.5 (3219)

$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

Alejandro

Dined on 1 Sept 2024

Aldo the server was very articulate and attentive. Overall decent waiter. Wes the Bartender was outstanding and made the experience great with the outstanding cocktails he was cranking out. 10/10 would recommend. Also I stole the waiter Aldo’s pen by mistake. Please reach out if he wants it back. :(

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Harry Caray's Tavern - Navy Pier

4.0

4 (940)

$30 and under

American

Gold Coast / Streeterville

About the restaurant

Located near the main entrance to Navy Pier, Harry Caray’s waterfront location, outstanding smoked barbecue, great selection of local craft beer and a world-class collection of sports memorabilia combine to create the ultimate Chicago dining experience. Guests are treated to dry-rubbed meats that are smoked for hours over hickory for maximum flavor and tenderness. The menu also offers salads and burgers. The carefully curated craft beer list features hard to find local gems along with many fan favorites.

Harry’s patio offers the perfect place to enjoy the beauty of Lake Michigan and the excitement of Navy Pier. HDTVs throughout the restaurant and around the bar provide great viewing of all major sporting events. Harry’s boasts an impressive roster of celebrity partners including Patrick Kane, Ryne Sandberg, Richard Dent and many other of Chicago’s biggest athletes, Hollywood stars and radio personalities.

Top review

Emily

Dined on 23 Aug 2024

Santa Fe Salad really good and gluten free . Recommend

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Experience

Chicago Fire Pier to Pitch Tailgate

Experience

Bears Tailgate September 29 vs Rams

Experience

Bears Tailgate October 6 vs Rams

Pizano's Pizza & Pasta - Madison

4.6

4.6 (280)

$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

Barbara

Dined on 29 Aug 2024

Her server was great. Food was great. We sat outside. It was really nice.. the street was a little loud, but it added to the Chicago experience. They gave us a scrumptious free birthday dessert too.

The Black Barrel Tavern

4.7

4.7 (140)

$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

Luncher

Dined on 22 Jul 2024

Service was outstanding. Had a nice comfortable feel.

Harry Caray's Italian Steakhouse - Rosemont

4.5

4.5 (2598)

$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

JOHNvip

Dined 2 days ago

Very nice evening, good food, great service , pleasant ambiance.

Paisans Pizza - Berwyn

4.4

4.4 (163)

$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

OpenTable Diner

Dined on 4 Jul 2024

Our meal, service, the ambiance and friendly service were perfect.

Remington's

4.6

4.6 (3159)

$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

Michelevip

Dined 5 days ago

Consistently excellent service & delicious food . Love the ambience and staff, we are happy to be regulars here!

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4.4

4.4 (217)

$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.

Top review

Diane

Dined on 27 Aug 2024

Server was excellent and very attentive to our table

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 23 Jul 2022

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

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