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Located in the Midwest, Chicago – known as the “Windy City”, is the third-largest city in America. It’s well known and famous for being a fun and exciting place to visit for both interesting attractions and incredible nightlife. Even if you only have a couple of days to spend, we’ve planned a route which is perfect for taking in the sights during the day, and the city’s vibrant nightlife after dark.


On the top of our list

Make your way down to the river and take a cruise through the centre of the city. You have lots of options on how to do this but we’d advise taking the Water Riders Kayak tour which is slightly harder work than your average tour but is a lot of fun.  This is a cool opportunity to paddle through the heart of downtown Chicago with a ‘duck’s eye view’ of the city. It’s a pretty amazing way to explore the city without having to deal with the busy streets.

Another great option is to just sit back and enjoy onboard the Seadog Speedboat Tours. This will give you a traditional tour with a twist – as soon as you hit Lake Michigan the speed cranks up to a whole new level.

Back on dry land head to the Navy Pier, this is a 50 acre playground of entertainment built in 1916. Ride the famous Ferris wheel, get scared on the wave swinger or have a round of mini-golf. It’s the perfect place to have some time out with friends.


Feeling peckish?

Head to Portillo’s on W.Ontario Street, a cult classic and home of true Italian Beef or Chicago dog. This is a famous chain in the mid-west and whilst it’s not the healthiest option, it is most definitely one of the tastiest.

For breakfast and brunch lovers, we’d head to The Bongo Room on North Milwaukee Street. From a Chocolate French Toast Tower to Eggs Benedict, you’ll find something to your taste and the portions are big – almost too big! Well, almost…

For a tasty lunch, it’s time to head for one of the most famous Chicago traditions and try real deep dish pizza. There is a lot of debate as to where does the best pizza, but we’d head to the place where it all began, Pizzeria Uno on East Ohio Street. The city’s deep dish pizza specialists since 1943.

Another great option for meat lovers is to head to Smoque. This is a great value and tasting BBQ restaurant, we would go for half a slab of St Louis Ribs, coleslaw and two sides and it comes in for just $15!!

If you’re looking for a nice burger, we would go to the Billy Goat Tavern and Grill. This is one of Chicago’s most famous and colourful burger bars. The food is quick and cheap and there is always a great atmosphere in the restaurant that has had lots of famous customers


One for the Sports fans

This is easy!  Your first stop is Wrigley Field, home of the Chicago Cubs. This is one of the most iconic sports arenas in America and if you are here on the weekend you should definitely catch an afternoon game. If you’re not so lucky, there is a lot of fun to be had in and around the stadium, like at the Museum of the history of the Cubs, or just have a break in some of the local fun bars and cafes.

If you’re an American football lover and you’re there in season, go see the Bears at the new Soldier Field. The Blackhawks hockey team play at the United Center (the largest arena in the US) or if you want to see where the great Michael Jordan played, then see the Chicago Bulls.  They also play at the United Center!

Soccer fans can go and watch The Fire.  Find out which famous players play there and enjoy an MLS game!


Feeling Brave?

Head to the Willis Tower, once the tallest building in the world, head up to the Skydeck and see Chicago from over 1300 feet up in the air. If you’re brave enough, look down through the glass floor that overhangs the building and gives you a look straight down.


Relax in the Park

To have a relax and a great time, head to Millennium Park. This is the pride and joy of Chicago – there are lots to do here. Why not head to the beach for a couple of hours and take a dip in Lake Michigan?

At the Millennium Park, see one of the 500+ free events held every year, including concerts, festivals, dance and theatre performances. Have your photo taken with the famous mirrored bean which has become a much-loved sculpture by the people of Chicago.


After Dark

It’s time to head to the House of Blues. This is a world-famous venue with a great party atmosphere with live Jazz and Blues Music. Dance and have fun for the entire night here, or there are plenty of fun bars and clubs in the vicinity.

When it comes to bars and clubs, you can go on as late as you want but if you’re up for a new venue, we would head to the Lincoln Park area of the city. It’s full of Chicago’s young party-goers and college students. There are some amazing places to hang out and have fun like the Store, the Beaumont or the Apartment, which are great places to have a drink.


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