Are you looking for a holiday destination where you can either embrace or escape the “chilly” weather? Then you may want to consider Chicago, Illinois and Sydney, Australia, two cities literally on opposite sides of the globe. Although they may seem worlds apart, they simultaneously have much in common. As the US moves from fall to winter and Australia moves from spring to summer in October and November, we thought it would be fun to compare these two iconic cities. Here is our list highlighting some of the best things they both have to offer.

Chicago: The Windy City

Modern Luxury At The Gwen

When looking for superior hotel accommodations in the “windy city” be sure to book a room at The Gwen, a Luxury Collection Hotel, Chicago. It elegantly integrates modern decor with vintage charm and boasts a desirable location on the Magnificent Mile. You will be near the city’s most exclusive retailers, its finest dining establishments and the most popular attractions and landmarks. Situated in the historic McGraw-Hill Building it has 300 guestrooms and 34 sophisticated suites with terraces, living rooms and stunning city views. Dine at the gourmet restaurant, enjoy cocktails at the terrace bar or relax in the impressive grand lobby lounge.
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Chicago Style Pizza

Chicago-style deep dish pizza

A preference for New York or Chicago style pizza is a fiercely debated topic in “food circles,” but you don’t want to miss an opportunity to try Chicago’s version for yourself. Famous for the deep-dish variety, there is no shortage of places to satisfy your cravings. For the ultimate foodie experience, head to one of the multiple Giordano’s locations and order a 3-6 pound Stuffed Pizza. It has a base crust layer, followed by a thick layer of mozzarella, then another layer of dough, followed by toppings such as meat, vegetables, more cheese and then sauce. Way more than your average pizza, this mouthwatering Chicago treat is in a class all by itself.

Chicago River & Riverwalk

Often referred to as one of the greatest feats of modern engineering, the reversal of the Chicago River is something you want to witness when you visit. Go on a Chicago Riverwalk & History Tour to discover the birth of the city, hear stories of vast fortunes of the elite, learn about the infamous “Chicago fire” and get the incredible facts about how Chicagoans re-engineered the flow of their river. Alternatively go on an architecture cruise, a sightseeing tour, a speedboat, a sailboat or kayaking on the river. There is no better way to have fun and peel back the fascinating history of this vibrant city.

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Green City Market

One of the best things to happen to Chicago as part of the urban farming movement is the introduction of places such as the Green City Market. Touted as the cities first year-round market it usually takes place at Lincoln Park. They are committed to supporting local farmers and sustainable practices and you will have access to the best seasonal produce from a diverse range of local producers, chefs, and artisans. It’s not just fruits and veg, you’ll find seafood, meat, and other goods and you can even get involved by volunteering, taking a field trip, a class or a workshop.

Wrigley Field Food & Stadium Tours

If you’re a sports fan, no trip to Chicago would be complete without a trip to Wrigley Field, home of the famous Chicago Cubs. Depending on when you go in the fall or winter you may be able to book a stadium tour where you can visit the seating bowl, press box, Budweiser bleachers, clubhouse, the dugout and have an opportunity to take a photo in front of Wrigley Field’s historic ivy wall. If it’s too late in the season or too cold, go on a 2-hour food and walking tour of Wrigleyville which is next to the stadium. Eat a Chicago-style hot dog, a beef sandwich, a mini-cheeseburger and snap photos of this popular landmark which is the second oldest baseball stadium in the USA.

Midwest Beach & Sand Dunes

For a hidden gem that usually only the locals know, head 50 miles southeast of Chicago to the Indiana Dunes State Park. This sand dune park is the perfect unexpected day trip from the city. You will discover miles of trails, lakefront beaches, marshes, an off-road bike trail, tree graveyards along with plenty of sand dunes to explore.

Sydney: The Harbor City

Park Hyatt Sophistication

No matter where you are in the world, you know you’ve made a good decision if you find yourself at the Park Hyatt. The location in Sydney is uniquely positioned right on the water’s edge the harbor. You can soak in iconic views of the famous harbor bridge and the world renowned Opera House from the property. The hotel is in the central business, cultural and shopping district giving you unparalleled access to the best of everything. The accommodations are no less impressive with spacious rooms and suites that showcase floor-to-ceiling glass windows, private balconies with stunning views and 24-hour butler service. Spend your time relaxing in the lavish day spa, lounging in the rooftop pool or dining at one of the two in-house restaurants enjoying gourmet cuisine in a refined atmosphere.
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Sausage Roll Satisfaction

Sausage Rolls are an Australian staple and this classic meat-filled pastry is a satisfying comfort food. One of the best places to experience this beloved favorite is at one of the multiple locations of the Bourke Street Bakery found throughout the city. Try some innovative, savory variations such as versions made with chicken, lamb, spinach or eggplant. Without a doubt, the traditional Pork & Fennel or the Beef, Beer, Bacon & Cheese Sausage Rolls are the real showstoppers.

Sydney Harbor Tour

It’s not an exaggeration to say that without its famous harbor the Sydney we know and love today probably would not exist. Surrounded by hundreds of kilometers of shoreline, national parks and historic sites this is home to the legendary Sydney Opera House. Ride the ferries, go kayaking or spend the day relaxing on a chartered yacht or book a tour where you can dive into the magical history of the city. Alternatively, venture out on foot and explore the harbor or spend the evening on a dinner cruise.

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Seafood At The Fish Market

Seafood and Sydney go hand-in-hand and the Sydney Fish Market is where locals and tourists alike go to sample the freshest catch of the day. Promoting sustainably caught seafood, the market showcases 6 wet fish retailers who offer Australia’s most extensive variety of fresh seafood. You will find numerous restaurants and cafés, bakeries, butchers, gourmet delis, a greengrocer, a bottle shop and even a fishing supplies store. While visiting be sure to take a class at the Sydney Seafood School Cooking, or go on a seafood-focused tour.

Olympic At ANZ Stadium

The ANZ Stadium was built in 1996 primarily for the Olympic Games in 2000. The ANZ Stadium holds a special place in the hearts of sports fans throughout the world. When visiting go on either the “Gantry Walk” tour or the “Explore” tour that gives you unrivaled access to exclusive, behind-the-scenes areas. This is one of the best ways for sports fans to spend a day and learn about the fascinating history and operations of this 83,500 seat stadium.

Aussie Beach Day

While all the tourists are flocking to Bondi beach, locals prefer to head to a hidden gem named Balmoral Beach located on the North Shore of the harbor. Often touted as one of the prettiest beaches in Sydney, it has everything you could want including a boardwalk, netted swimming baths, a playground, picnic tables, and even an adjacent skate park. Additionally, this beach boasts a great natural shallow splash pool that’s perfect for toddlers. The fish and chips are legendary in this area and insiders recommend the Bottom of the Harbor Fish & Chip shop for the ultimate experience.

Melisa Richter author profile

Melissa is a passionate foodie, travel writer, and editor working in media internationally and in the USA. She has lived in Bangkok since 2004 and has a background in the travel industry. Melissa’s writing has been published globally in many prestigious online and print magazines for over a decade. Her motto for life is “You cannot live or love well if you have not wined and dined well!”