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15 Cool Things To Do On A Weekend Trip To Chicago (5 Not Worth The Time)

If you love the push and pull of the big city, but crave the friendliness and generosity you only get from small towns, you may be surprised to learn that Chicago has it all!

Big city buildings and small town smiles make up the beautiful windy city of Chicago. Having travelled there for a long weekend last year, one of the first things I said to my travel partner was, "We have to come back!" We were overwhelmed by how comfortable we felt in the city, how welcoming the people were, how cleans the streets were, how delicious the food was, and how easy it was to get around in the city.

Pack a hairbrush, because your hair is going to get tangled in the wind.

Chicago has something for everyone. It's perfect for the outdoorsy type, who prefer parks and walking trails. It's great for foodies, looking to try new dishes and flavours. And, of course, it's great for sports fans, eager to catch a game with one of the city's many major league teams.

To make your trip memorable, there are some places you need to see, and a few you should avoid, in order to maximize your time in the city. We're looking at the best the city has to offer, as well as a few things that aren't worth your time or money.

20 See the bean (A Must)

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As crazy as it sounds, one of my favorite activities from my weekend in Chicago was visiting Cloud Gate, aka the bean. My partner and I loved it so much we went back again for a second visit. It's hard to say what's so appealing about a giant blob of reflective metal, but in a way it feels like the heart of the city, and tourists from across the city gravitate there naturally.

If you like crowds, you'll like the bean. People watching, photobombing and soaking up the sounds of happy travels are a few of the things you can expect to do around the bean.

Walking under the bean feels a bit like passing through a fun house. If you're lucky enough to snap a photo without a dozen other heads behind you, it'll be a rare commodity. But that's part of the fun. In the day, the city sparkles in the bean's reflective surface. At sunset and at night, it seems to glow. Whenever you visit, the view will be picture perfect.

19 walk around millennium park (A Must)

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If you visit the bean, you need to give yourself the extra time to explore the rest of Millennium park. The Bean is great, but it's only the tip of the iceberg. They have other types of interactive art, including Crown Fountain just a few steps away. Crown Fountain is book ended by two larger than life faces projected on LED screen, which spout water from their "mouths". Kids can play around in the reflective pool and parents can either be creeped out or thankful for the extra set of digital eyes on their child.

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And of course, no trip to Millennium Park is complete without a visit to the Jay Pritzker Pavilion, aka the field covered in what looks like a stainless steel web and the stage somewhat reminiscent of the Sydney Opera House, with massive curving plates. If you're lucky you and 10,000 other visitors might be able to catch an open air concert.

18 indulge at a fancy restaurant (A Must)

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Chicago has some of the best food around. From Michelin Star restaurants, that'll cost you a month's rent, to more reasonable restaurants where you can manage to find a seat without a reservation, there's something for everyone in Chicago.

It's easy to hop into a pub style restaurant and order a deep dish pizza, but there's only so much greasy food you can eat in a weekend. If you're looking to class up your evening, find a nearby restaurant with good reviews, there are bound to be dozens, and get a last minute reservation.

We were lucky enough to go two for two as walk-ins at both an upscale Italian place and a classy seafood restaurant. We felt like imposters as we sipped our decadent drinks to the music of a live pianist. Treating ourselves so well was one of the highlights of the weekend!

17 go shopping along Michigan Avenue (A Must)

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It's hard to avoid Michigan Avenue, aka the Magnificent Mile, when you're making your way across Chicago. The street is massive, it passes through the heart of the city, and offers an easy way to get from the loop up to some of the better shopping areas.

Chicago may not have the glitz and glamour of New York's Times Square, but the stores are nonetheless impressive. Usually multiple stories tall, countless big brands are featured along Michigan Avenue, as well as family friendly stores like Disney (which sells adorable Chicago themed Mickey dolls and t-shirts). It's a definite must, even if you only window shop.

16 take a picture by the fountain (A Must)

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Buckingham Fountain offers tourists one of the best views of the city. Located in Grant park, a hop skip and a jump away from Millennium Park, Chicago's most famous fountain is something to see!

It's one of the largest fountains in the world and hold more than 1.5 million gallons of water. Between 8:00 am and 11:00 pm, from April to October, Buckingham Fountain puts on a water show every hour on the hour. The twenty minute show includes lights, music, and jets that shoot water up to 150 feet in the air. If the massive size of the fountain wasn't enough, the show will make your day. But make sure you visit during peak season, you don't want to be like me and walk all the way to the fountain just to find out it's turned off!

15 Walk along State street (A Must)

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State street was one of my favourite undervalued areas of Chicago. Everyone talks about the Magnificent Mile, but if shopping isn't your thing, you'll feel much more at home on the smaller, friendlier, more picturesque, State street.

Coming off the "L" train from the airport, State Street was one of our first glimpses of Chicago. There's everything you want, shopping, restaurants, and best of all views. The theatre sign is just begging for a photo op, and State Street bridge gives you a great view of the river.

14 try deep dish pizza (A Must)

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No trip to Chicago is complete without deep dish pizza. Bring your appetite, because these things are filling! It's basically a pie that calls itself a pizza. There's a lot of cheese, a lot of sauce, and you'll need a fork and knife (there's no way you can pick up a slice of this pizza without getting messy.

Keep an open mind, though. If you're a thin crust lover like me, your palette won't know what's happening, but it's worth a taste. Maybe I picked the wrong place, maybe I picked the wrong flavor, but all I know is, I was overwhelmed and couldn't finish my plate!

Maybe split with a friend if you're a first timer like I was.

13 visit the Art Institute (A Must)

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When you're in Chicago, you have the privilege of being in the same city as some of the world's greatest art. To pass that up would be ridiculous.

The museum is one of the oldest and largest in the United States, which means it's attracted art from renown artists across the world, including Picasso, Rembrandt, Renoir, Van Gogh, Monet and more.

Even if you're not a museum fan, you'll be surprised at how many famous paintings made their home in Chicago.

12 walk along navy pier (A Must)

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Many people say Navy Pier has lost it's charm and it's a waste of a walk to get there, but I disagree. Navy Pier offers a different perspective of Chicago, away from the city centre and by the water's edge. That means you get a beautiful view of the city skyline, and the view of the pier is not bad either!

There are some fun places to eat, delicious smells, and of course the Ferris Wheel to gawk at. You could ride it, but that's likely not worth the cost. Instead, opt for a nice photo in front of the Ferris wheel.

On the other hand, Chicago is the birthplace of the Ferris Wheel, which was introduced in the city at the 1893 World's Fair and was an engineering marvel at the time. For that little historical tidbit alone, I felt compelled to see the city's current Ferris Wheel when I visited.

11 take an architecture river cruise (A Must)

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Everyone I spoke to before my weekend in Chicago told me the same thing: "take a river cruise." That's because the city was built around its river, and all the best sights and views are from the water.

The architecture cruise is actually really enlightening. You get a little history about some of the cities best buildings, and you'll be snapping photos nonstop. Plus it's really relaxing. There's a lot to see in Chicago, and I probably walked at least 20,000 steps during my weekend visit. The river cruise will give your feet a rest, and is sure to be the one thing you recommend to your friends when they visit the city after you.

10 Chill by the river (A Must)

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When I travel I like to eat and I like to drink, because so much of a country or city's culture can be represented in what you consume. In this case, there's an incredibly cute winery (more like a bar) by the river, where you can have a relaxing drink by the water while you look out at State Street bridge and some of the city's best architecture behind it.

While trying to find this place, we must have walked the street a dozen times, going in all directions. Finally, it dawned on us, that we needed to get off the street, walk down the steps, and get onto the riverwalk area. We were so relieved to find the place, and it was so worth it!

9 visit Wrigley field (A Must)

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Take me out to the ball game, take me out with the crowd! Chicago is home to some impressive major league talent, but the Cubs at Wrigley field take the cake. People come from across the continent to see a game at Wrigley park, and even if you're not a baseball fan the atmosphere is infectious.

In Chicago, it's just as popular as the other states to get yourself a hot dog during the game, but for some reason, ketchup and hot dogs don't mix in Chicago. Instead, the ballpark franks are topped with yellow mustard, green relish, chopped onions, tomato wedges, a pickle, sport peppers and celery salt. If you add ketchup, it goes against the true Chicago way!

8 visit the free zoo (A Must)

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There are never enough hours in a day and days in a weekend to do everything you want to do in one short visit, but when I heard "free" the zoo shot up to the top of my list. After shopping and eating it's nice to find a place where you can have a fun filled afternoon without over spending.

No tickets needed, just walk through the gates and take advantage of the zoo's many shows, exhibits and sights. You may even catch a wedding or two, as it's a popular venue for brides.

There are more than 200 different species in the zoo, and with one of the country's biggest conservation programs, the animals are well cared for.

7 spend time at the beach (A Must)

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Did you know Chicago had beaches? It may not be California, but Chicago's beach is the best way to turn your city-centric weekend away into something with a more relaxing down-south feel.

There are actually several dozen beaches around the Chicago area, some of them walking distance from the city centre. Depending where you go, you can enjoy a drink on the boardwalk, rent a kayak and go out on the water, or simply sunbathe on the sand.

If you spend an afternoon by the beach and an evening in the city, you'll really get to feel how diverse and multifaceted Chicago can be.

6 watch a game (A Must)

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We already mentioned how Wrigley field is a must, but there are several other teams to get tickets for as well.

Chicago has a team (or two) in every major league. You have the Chicago Cubs and White Sox in baseball, the Chicago Bulls in basketball (with some major Michael Jordan pride), the Blackhawks in hockey and the Bears in football. Whatever sport you like, whichever team you support, Chicago is a sport city and there's a huge fanbase for their teams.

If you catch a game, anything from soccer to hockey, you won't be disappointed.

5 Avoid O'Hare Airport (Not Worth It)

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There are two ways to fly in to Chicago, the way you should take and the way you should avoid with everything you have!

Chicago's O'Hare airport is notoriously one of the worst airports in the USA. It's huge, it's crowded and it's slow. And worst of all, flights are often delayed or cancelled, more so than other airports.

It may be cheaper to fly in to O'Hare, but it's not worth the savings.

Chicago's second airport, Midway, is closer to the city, much smaller and way easier to pass through. Coming from Canada, I was shocked at how quickly I passed through customs. There was no line, no waiting, nothing! Within fifteen minutes were were outside. It was the easiest most pleasant airport experience of my entire life, and I will recommend Chicago's Midway airport over O'Hare for the rest of my life.

4 skip the Willis Tower skydeck (Not Worth It)

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Chicago was once home to the tallest building in the world. For almost 25 years, Willis Tower, aka Sears Tower, was the tallest building. But then buildings started getting taller and taller across the globe, and now Chicago's skyscraper is the 16th tallest building in the world and the second tallest in North America.

Even without the title of word's tallest building, the tower attracts more than 1 million visitors each year, and its skydeck has become a little too popular.

People wait hours in line to get up to the top of the tower and take a picture on the clear floor. It's definitely a unique experience, but it's just not worth the wait, especially when there is so much else to see in Chicago, from other equally beautiful angels.

3 Avoid "Broadway" shows (Not Worth It)

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Chicago is sometimes called Second City, as in, the second best city after New York. In the world of Broadway though, Chicago can come first, as in, the big broadway musicals test the waters in Chicago before heading to the big apple to set up camp on Broadway.

But when you get tickets to a Broadway show in Chicago, it's pretty much sacrilege to the city. Chicago has its own unique and worthwhile theatre and comedy scene, and seeing a Broadway show, intended for New York, while in a city with so much to offer itself seems a waste.

Why not visit a local theatre production instead, or visit Second City comedy club and see why Chicago is number one when it comes to improv and stand up.

2 avoid colder seasons (Not Worth It)

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I made the mistake of visiting Chicago in November and it was definitely disappointing. We still fell in love with the city, but we passed so many booths, shops and attractions that were closed for the season it was heart breaking. Most heart breaking of all was that Buckingham Fountain was turned off for the winter and we missed out on one of the city's highlights.

It may be fun to see the city all snowy, or decorated for Christmas, but it's far better to see Chicago in all it's glory, in the summer. There are more activities to do and see outside, festivals, shows, concerts, you name it. In the colder seasons, everything is a little quieter and a little more, how can I say it nicely...dead.

1 Don't get a hotel in the loop (Not Worth It)

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If you're going to Chicago, it will be tempting to get a hotel room in the Loop. It's close to everything, you'll say. There are some good deals, you'll convince yourself. But no! The Loop is just a small part of Chicago. By getting a room down the Magnificent Mile or in one of the suburbs even, it will force you to walk a little farther and explore a little more. And with so much to see and do in Chicago, you're really limiting yourself if you spend all your time in the Loop.

Plus, what I discovered is that all the best restaurants are outside of  the Loop anyway! So why bother when you'll need to take the L train or a taxi across the river to eat.

Save yourself the money and opt for something on the outskirts. You'll thank me later.

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