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Don’t be shy when “Chi-Town” calls your name. Despite the rumours of cold, windy mornings, the largest city in Illinois offers a warm Midwestern welcome to travellers seeking sporting events, performing arts and a saucy piece of pizza pie. As a major political and media hub, Chicago has a serious side, but don’t underestimate the opportunities for fun and belly laughs that await you on Chicago holidays.
With attractions sprinkled all over the city, from Wrigleyville to Hyde Park, hotels in Chicago are available close to the top sites on your itinerary. You can even book accommodation near Lincoln Park for instant access to the Museum of Contemporary Art Chicago and your new furry or feathered buddies at the Lincoln Park Zoo.
First things first, traveller. Let’s go out to the ballgame. Even if sports aren’t your thing, you’re a baseball fan when you’re in Chicago. Pick up some blue and red face paint and grab seats at Wrigley Field for the next home game. Once you’ve shouted with the locals, check out the bean-shaped Cloud Gate sculpture and jog through Millennium Park, because nothing puts your life into refreshing perspective like a reflective legume.
If you want to visit Chicago’s biggest hitters right off the bat, get a Chicago CityPASS and tour top attractions like Shedd Aquarium and The Field Museum. OK, we’ll stop with the baseball puns.
North of Millennium Park, the Chicago Riverwalk is the perfect place to eat and shop to your heart’s content, surrounded by gorgeous views and luxurious Chicago hotels where you can relax after a long, tiring day of…being on holiday. When you’re ready for more, make your way up the Magnificent Mile to the vintage Gold Coast neighbourhood for an arvo at the beach.
Next, catch a comedy show at Second City Theater in nearby Old Town. Once a nickname for Chicago’s status as the lesser of the country’s biggest cities, “Second City” is now synonymous with the funniest people of the past century, including Tina Fey, Alan Arkin and Gilda Radner.
Breeze into the “Windy City” via two major transit hubs: O’Hare International Airport (ORD), located about 17km northwest of downtown, or Chicago Midway International Airport (MDW), just 11km to the southwest. With an efficient light rail system and bus routes weaving through busy streets, you can easily get from the airport to popular attractions and accommodation in Chicago with public transportation. If you want to tackle traffic like a local, pick up some wheels with one of our car hire options and hit the streets.
Between April and October, Chicago trades in its blustery reputation for warm breezes and stylish sunnies. That’s when the events calendar is hopping, so consider booking Chicago accommodation during this time if fun in the sun is important to you—how could it not be?
As summer winds down, the only thing moving at a slower pace are the smooth tunes crooning from the Chicago Jazz Festival every September. Come October, there’s a party a’brewin’—the annual Chicago Beer Hoptacular, which is a celebration of exactly what it sounds like. Bottoms up!
You’ve no doubt heard that Chicago can get chilly from November through February, but these cold months are among the city’s most beautiful. The winter wonderland glows during the Magnificent Mile Lights Festival and other celebrations in November. To keep yourself warm during a brisk November holiday, join the singing, dancing and art-making at the annual Native American Pow Wow.
If you’ve ever wondered how Chicago got its motto, “urbs in horto”, then you’re not alone. If you’ve ever wondered what “urbs in horto” means, you’re really not alone. The English translation is “city in a garden”, and Chicago sure does live by its slogan. The streets are lined with skyscrapers, but these scrappy Midwesterners will have their green spaces, doggone it. In fact, you can take a breath of fresh air surrounded by flora galore on the rooftop of City Hall!
Closer to sea level, the Alfred Caldwell Lily Pool is a peaceful—and watery—oasis in already-gorgeous Lincoln Park. You’ll definitely want to snap some selfies in the stone-lined pergolas. But be advised, there is a high probability that you will either witness a marriage proposal or get the strange urge to make a lifelong commitment in this lovely garden. Hey, it happens.
To run through wide open spaces in the middle of the big city, lace up your trainers and head to the Burnham Centennial Prairie, a nature preservation area on the Chicago Lakefront Trail. Tall grass grows in the breeze and wildflowers take over the sprawling fields. Located on the edge of Lake Michigan and close to the busy Loop, the Lakefront Trail is lined with some of the best places to stay in Chicago.
When you hit the windy streets of “Chi-Town” it’s hard not to see the tallest building in the city, but make sure you have your eyes looking up when you’re wandering through the west side of the Loop, especially if you have just one day in Chicago. “Why?” you ask? Because that’s where you’ll find Willis Tower (aka “Sears Tower”, aka “442 metres of awesome”), which was considered the highest building in the world until 1998.
When you’re done staring, get out of the middle of the footpath and head to Navy Pier to graze on some of the best food in Chicago. From shopping on the boardwalk to stuffing your face with smoked smallmouth bass in waterfront restaurants, your arvo will be off to a good start. Stick around for a concert or hop on a cocktail cruise to top off the perfect holiday in style.
Ready to make your way through the “Toddling Town”? Book hotels and flights to Chicago with Wotif. We’ve found great travel deals, and we’re really good at sharing.
Need insider tips on must-see attractions in Chicago? Check out our Chicago travel guide!
Hotels in Chicago start at AU$75 per night. Prices and availability subject to change. Additional terms may apply.