It’s often referred to as the Windy City, and is home to nearly 10 million people making it the third-largest city in the United States.  Chicago may, or may not be at the top of your list when considering all of the holiday travel options this season, but when considering your appetite for holiday cuisine, your cravings to celebrate and feast in grand holiday merriment may actually be the deciding factor.

Chicago, Illinois has historically laid claim to a large number of regional specialty restaurants and styles of food, all of which reflect the city’s ethnic and working class roots, making it one of the most diverse culinary cities in the world. From the deep dish pizza, to the Chicago-style hot dog, the history city has always laid claim with these well-known classics.  But in the last several years there’s been a spike in burgeoning trendy new restaurants landing all over the city, adding Chicago’s rich history and serving as a beacon for many great culinary transformations that has inspired hundreds of chefs and culinary professionals throughout the United States.

If you’re looking for a unforgettable culinary holiday travel experience, Chicago should be at the top of your list. Austinites planning to visit the Windy City this season better be prepared to bundle up as you’ll need more than a wind breaker and yoga pants you can typically get away with here in Texas. Chicago’s temperatures are consistently reach freezing conditions, which is obviously something we don’t experience often in Austin.  But don’t let the cold weather spoil your fun, it is after all, part of the romantic charm Chicago has to offer during the holiday season.

Photography by Choose Chicago. 

A Few Tips


Whether you’re a seasoned Chicago vet or a first time visitor, you’re in for a special treat.  Chicago is an amazing city filled with a never ending list of fun activities to enjoy, making the perfect metropolis to celebrate the holiday season.  Before you jump on a plane and get lost in the big city here’s a few important tips you’ll need to survive your wintry quest.

  • Pull out your Winter Gear – The weather outside may be frightful, but don’t let that be a reason to prevent you from enjoying the city.  Temperatures will typically drop to below zero during the winter months, so invest in a decent winter coat and appropriate winter-wear for the duration of your trip.
  • City pass logoInvest in a City Pass –  You’d probably rather spend more of your money on your shopping, entertainment and dining instead of all of the “touristy” attractions, but if you’re new to Chicago, you don’t want to pass up the famous landmarks and activities that make visiting Chicago such a fun experience.  The Chicago CityPASS will get you access to Chicago’s most popular attractions all for one set price instead of individual ticket prices at each location.
  • Pick up a Transit Pass 
    CTA 'L' Train

    CTA ‘L’ Train

    The L-Train system and the Meta rail are by far your best options of transportation.  Chicago has one of the most efficient and reliable public transportation systems in the world, so familiarize yourself with the transit maps and schedules, which you may access using their app or via Google Maps on your smart phone.  A one-day pass cost $10, three-day pass is $20 and seven-day pass is $28. Your best bet is to invest in a $5 Ventra Card which are available in the vending machines in all stations. The card allows you to refill credits which is valid on both the “L” train and the metro bus.

  • Chicago food planetChicago Food Planet Tour Pass – In a city as big and diverse as Chicago, there are more culinary destinations than you can possibly manage to digest all on one trip. The Food Tasting and Cultural Walking Tour includes tasty food and drink tastings in some of the city’s off-the-beaten-path neighborhoods. You’ll walk away with a full belly and new culinary perspective, filling up bites and sips from famous local restaurants, bars and ethnic eateries with an insiders view into the culture, history and architecture that defines Chicago. Tickets start at $48 per adult, a fantastic bargain for the amount of food you’ll devour on this tour.



 Connie’s Pizza

Connie’s is one of Chicago’s best kept secret for delicious Italian dishes and pizza since 1963. Their award winning design of an 1800s style warehouse and flavorful Italian food has made them an Open Table Diners Choice winner, and earned recommendations from Trip Advisor and the infamous Michelin Guide.

What to Order

Connie’s Original Pan Pizza: The original Connie’s panned pizza that has made them a Chicago favorite for almost 50 years.

Deep Dish: A Chicago favorite similar to the original panned pizza with just an extra amount of goodness. The deep dish is legendary, being featured at festivals and sporting venues throughout the Chicago land area.

2373 S Archer Ave

Chicago, IL 60616

connie's pizza


Pizza East

Pizza East is a modern spin on a pizzeria with their signature ciabatta-style dough, Italian mozzarella and locally-sourced meat.  Their passion for sourcing quality ingredients is at the heart of everything that comes out of their wood ovens.

What to Order

Wood Fired Pizzas: Burrata, tomato, black olives. + Cherry tomato, olive oil, buffalo mozzarella + Four cheese, black truffle

113-125 N Green St

Chicago, IL 60661

Pequad’s Pizza

Since 1970 Pequods became the best known secret for Pizza in the northwest suburbs. Now set in the Lincoln Park area since 2006, this famous pizza joint has become one of the best spots for families, couples and groups with two floors of seating. They’ve developed a local and national pizza following for their unique pan pizzas and welcoming atmosphere!

2207 N Clybourn Ave

Chicago, IL 60614

Publican Quality Meats

Publican Quality Meats has some of the most delicious, Chicago-style hot dogs, sandwiches and deli meats in the city.  Chef Paul Kahan’s West Loop butcher shop & cafe, has a rotating menu which includes everything from delicious salads and charcuterie, as well as their selection of house cured meats.  The tight space has communal seating and is constantly crowded, which is a testimate to their delicious menu.

825 W Fulton Market | Map
Chicago, Illinois 60607

Parson’s Chicken & Fish

Located in Chicago’s Logan Square neighborhood, on the beautiful Humboldt Boulevard, Parson’s Chicken & Fish embraces drinking, eating, and general good times.  A project of the Land and Sea Dept., Parson’s Chicken & Fish affectionately references the chicken and fish eateries prevalent to the West Side of Chicago, and found in cities, coasts and regions across the country – the sorts of places that offer affordable eats quickly, and that satisfy big appetites.

2952 W Armitage Ave

Chicago, IL 60647

Photo by Clayton Hauck for Parson's


 Photo by Clayton Hauck for Parson’s

The Girl and The Goat

Executive Chef and “Top Chef” winner Stephanie Izard’s Girl & the Goat is one of Chicago’s most popular restaurants, serving a family style menu of tasty, bold small plates with global influence in a fun and lively setting. The menus are extensive and have a little something for everyone to help create the perfect dining experience for every guest.  They also offer a selection of wines from around the world with a focus on small producers, a rotating list of craft beers with a celebration of local Chicago breweries and a list of fun cocktails.

809 West Randolph Street | Map
Chicago, Illinois 60607


The winner of a prestigious 3-star Michelin award, Grace offers one of the finest dining experiences you’ll ever receive.  Grace is a modern, new-American restaurant that offers a 9-course tasting menu starting at around $235 per person. The esteemed restaurant is the very definition of perfection in dinning experience.  Excutive Chef Chef Curtis Duffy and General Manager Michael Muser have created a dining journey of distinction, as you’ll discover flavors and pairings are among the greatest in Chicago’s great culinary landscape. If you’re planning a visit to Chicago

652 W Randolph St

Chicago, IL 60661


Trenchermen is a hip, modern American dining restaurant that’s inspired by the history and local neighborhoods of Chicago with a distinctly forward theme focused on craft dining and creative cocktails with a vintage vibe. In the 1920’s, the building that plays home to Trenchermen was originally opened as the Luxor Russian Baths.  Fast-forward to today, the building is now classified with the second highest rating on the Chicago Historic Resources Survey and home to one of the best restaurants in the Bucktown area. The dining room is unassuming yet elegant, and inviting.  The dinner menu allows you to plot your own course from a few small plates to a $50 four-course prix fixe meal.

2039 W North Ave

Chicago, IL 60647

photos by Hayden Walker

Fat Rice

In perhaps one of the most adventurous dinning journeys we’ve ever experienced, Fat Rice should consider itself one of the most progressive restaurants in Chicago.  This constantly‑packed hot spot in Logan Square features one of the most unique dinning experiences you’ll see anywhere in the world.  Chef Abe Conlon’s Portuguese fusion cuisine features flavors influenced from Asian-European unions of China, India and Southeast Asia. Fat Rice provides an exotic dinning experience filled with unique flavors and spices making it one of the most outstanding restaurants in all of Chicago.

2957 W Diversey Ave

Chicago, IL 60647

Read our REVIEW

Stan’s Donuts

Originally based in Los Angeles, Stan’s Donuts has become a Chicago favorite since Labriola Ristorante & Cafe owner, Rich Labriola brought the famous donut shop to Chicago. Stan’s specializes in old-fashioned doughnuts with chocolate or lemon glaze. It’s a donut lover’s paradise with so many mouthwatering choices to devour, you’ll need to live in a gym for the next week or so.  You’ll find large apple fritters and blueberry fritters, toffee cake donuts, chocolate cake doughnuts, buttermilk bars, and specialty donuts like the Nutella banana pocket, and maple caramel bacon pecan bar.  Stan’s has become the very definition of donut porn!

@stansdonutschicago We need you in Austin! Seriously! #Chicagodonuts #getinmybelly #foodporn #cfwfest

Glazed and Infused Doughnuts

Established in 2012 by acclaimed Chef and Restaurateur, Scott Harris, Glazed & Infused doughnut and coffee shops are fun and casual. All of the donuts are made fresh daily by hand, using whole and natural ingredients. The shop rotates flavors seasonally adding a little excitement to the menu to include holiday and specialty doughnuts. Our favorite was the Maple Bacon Long John doughnut which includes a large thick cut slice of bacon on top of a generous serving of maple frosting.

Hoosier Mama Pie Co.

Hoosier Mama Pie Co. makes sweet and savory pies, and quiches by hand using outstanding ingredients. They bake with each of the seasons in mind purchasing organic produce from local farmers with 10-12 different types sweet pies and 3-4 different savory pies as well as a quiche or two available each day. This little pie company was the biggest hit at this year’s Chicago Food and Wine Festival, as attendees consistently filled the line anxious to get their hands one of the adorable handheld pies.

1618 W Chicago Ave.

Chicago, IL 60622

Holiday Fun

Chicago Winter

Caroling at Millenium Park

Dscover a state-of-the-art collection of beautiful architecture, landscape design and art that provide the backdrop for hundreds of free cultural programs including concerts, exhibitions, tours, and family activities. In Millennium Park, you’ll find a new kind of town square this holiday season – a lively, spectacular gathering spot located in the heart of the city and a destination for Chicagoans and visitors alike.

cloud gate singing

photos by Choose Chicago and City of Chicago

Skating in McCormick Tribune Ice Rink

Kicking off Chicago’s winter season, the McCormick Tribune Ice Rink in Millennium Park will open on Friday, November 13, 2015 and will remain open through March 6, 2016, weather permitting. For the last 14 years, the rink has drawn more than 100,000 skaters annually and is free and open to the public. The rink, located on Michigan Avenue between Washington and Madison Streets, will still offer skate rental for only $12.


Millennium Park, McCormick Tribune Ice Rink
201 E. Randolph St.
Chicago, IL 60601

ice skating

102nd Christmas Tree

Through December 2015 – FREE

The City of Chicago’s 102nd Christmas Tree begins a new tradition this holiday season in Millennium Park near the intersection of Michigan Ave.

christimas in chicago -


Holiday Shopping

Find the best shopping in Chicago, no matter who’s on your holiday gift list, with this year’s holiday shopping guide. From outlet malls in Chicago suburbs to shopping downtown Chicago, there’s plenty to find for label lovers and bargain hunters alike.



The 900 Shops
Located at the north end of The Magnificent Mile shopping district, the 900 North Michigan Shops is a chic indoor shopping destination with 70 luxury stores such as Gucci, Montblanc, Coach, L.K.Bennett and Michael Kors, in addition to one of the best known department stores in the world, Bloomingdale’s.

The Shops at North Bridge
Spread throughout six city blocks, shoppers can explore 50 stores, such as BOSS Hugo Boss, Sephora, MAC, Louis Vuitton and more, as well as a flagship Nordstrom and 20 restaurants including the massive Italian emporium Eataly, Joe’s Stone Crab and The Purple Pig — all in the expansive North Bridge District.

Water Tower Place
With more than 100 shops, including Macy’s and a flagship American Girl Place, this spectacular, eight-level mall offers an array of retail options across all price ranges (from American Eagle Outfitters and Abercrombie & Fitch, to Adidas and Banana Republic, Pandora and Swarovski), as well as dining, spas and more.

Lincoln Park
For independent boutiques and high-end retailers, stroll down Armitage Avenue for a day of shopping. From upscale pet accessories to sophisticated home-décor stores to trendy fashion boutiques, this is the spot to shop for well-heeled gift recipients.

November 20-December 24, 2015
Deck the halls after a trip to this annual outdoor market, which celebrates the holiday season with German American traditions. Buy ornate, hand-blown glass ornaments, gorgeous nutcrackers, charming cuckoo clocks and other wooden handicrafts. You also can sip on hot, spiced wine, nosh on sausages and potato pancakes and sample many other German holiday delicacies.


W Hotel Lake Shore

photos by W Hotel

The W Hotel Lakeshore is the perfect spot to celebrate and relax during the holiday season.  The hotel overlooks the beautiful Lake Michigan and the Navy Pier, for a nearly all white and wintery view. You’ll enjoy the hotel’s modern and stylish holiday escape as you spoil yourself to a life of luxury  while visiting Chicago.  It’s only a 13-minute walk from Navy Pier and 4 blocks from all of the holiday shopping along the Magnificent Mile.

All rooms are stunning and come standard with Wi-Fi, 32-inch flat-screens, iPod docks, minifridges and 24-hour room service. Some suites add sitting areas with wall-to-wall windows with a panoramic view of Lake Michigan or the downtown skyline. Other amenities include an indoor heated pool with city views, a nightclub with live entertainment and an onsite spa. 

Add a dash of sparkle to your holiday style this season. Spend time in the heart of the city getting gifts for friends and family or a little winter wardrobe shopping for yourself.

  • $50 AMEX Gift Card
  • 15% discount card for Bloomingdales
  • Complimentary VIP Bloomingdale’s Wallet
  • Stay in an upgraded Spectacular room
  • Plus, 20% discount for services in Bliss Spa


For more tips and exciting ways to enjoy your holiday trip to Chicago, visit Choose Chicago, to enhance your experience with the best deals and guides available.


About The Author

Hayden Walker
Executive Editor | Co-Publisher

Hayden Walker is the Editor in Chief and Director of Operations for Austin Food Magazine

Related Posts

One Response