I haven’t blogged as often as I have wanted to these last few weeks, mainly due to time pressures and worries at work (that literally made me cry, no joke). Thankfully, we had a break to Chicago planned and it frankly could not have come at a better time. Sam and I were both exhausted so a little time out was really needed.

My brother lives in Chicago so I guess you can say that we’re pretty good at getting around; hopping on and off the metro and using buses, etc, is second nature. We’ve taken in all the sights this trip, but for those of you who aren’t au fait with Chicago and are thinking of visiting (it’s well worth it), then read on for my simple guide on what to see and how to get there.

Downtown Chicago
Famous for its skyline, shopping and sprawling parks, downtown Chicago is really the place to be. The metro system has a circle of stops known as The Loop, though the distances are definitely walkable.

There are a number of key sights to take in downtown. The John Hancock Centre is the second tallest building in Chicago and worth a trip up to the 97th floor. It has stunning views across the whole of Chicago and, being near the lake, takes in Navy Pier and Lake Michigan too. It costs $19 per person plus tax. The Willis Tower is the tallest building in Chicago and it does have a glass floor (for those keen on a selfie or two), but it’s away from the lake and close to the river and doesn’t have such impressive views.

From the John Hancock Centre you can really take your pick of activities as the city is walkable, (though do stop by the Cheesecake Factory at the foot of the building because it is literally the best cheesecake I’ve ever had). My suggested route would be to walk east a few blocks to the lake, stop for a bite of lunch on Navy Pier and then do an afternoon river boat cruise. The cruise goes up the river and takes in Chicagos’s architectural buildings and is quite informative and enjoyable, though it does cost $39 each (plus tax!)

If you head a few blocks further south you’ll get to Millenium Park, home to The Bean. The Bean is a famous metal sculpture which reflects the skyline of Chicago and is a must-do for a every first-time visitor.

Depending on what time of day you visit, I would recommend that you stroll through the rest of the gardens at Millenium Park and take in the visual fountains before heading across the road to the Athletic Association and up to Cindy’s bar. This bar is great late afternoon on a summer’s day – and you don’t have to be dressed up, don’t worry, it’s suitable for all forms of attire including walking shoes. Prices are not high and you’ll thank me when you enjoy a cocktail overlooking the park and the lake.

Further south
Heading a bit further downtown you’ll reach Grant Park which features the huge Buckingham Fountain. If you’re visiting in early May, like we did this year, they hold a cute fete in the early afternoon with a countdown to the turn on of the water. The fountain marks the beginning of the summer season in Chicago, when there are loads of music and food festivals to enjoy.

From Grant Park walk west a couple of blocks to the Washington Library. It is an impressively large red brick building with some lovely arty ceilings inside.

If you fancy venturing south even more, get on the green metro line and hop off after Roosevelt in order to visit the Clarke House. This is the oldest house in Chicago and survived the fire that ravaged most of the city. Tours are free and take place twice a day a couple of times a week, so check before you go in case it is closed.

Whether you are staying in the north or south, I would recommend that you take a walk along State Street and Michigan Avenue for a little shopping! State street is best for footwear – there are literally a dozen different shoe shops in only two blocks near the Lake metro stop. Michigan Avenue is home to the Magnificent Mile row of shops, some on the more expensive luxury side.

Near North
There is not as much to do in the north of the city, though the roads are wide and lined with pretty houses so worth a walk about. We get off at Fullerton metro stop on the red line and walk east several blocks to Lincoln Park and the conservatory. Both are free to enter and from the south of the park there is a wonderful view across to the skyscrapers of downtown. The zoo houses a polar bear, which I don’t much like as he is often agitated and is in far too small an enclosure really.

Whilst in Chicago you MUST take in a baseball game, even if you don’t understand the rules (we literally had no idea what was going on or who was winning when we went). The Chicago Cubs are based at Wrigley Field, at the Addison metro station (red line), whilst the White Sox are based down in the far south. You can get cheap seats only a couple of days in advance so don’t worry about booking ahead.

Heading further north from Addison takes you to Evanston. This is a lovely part of the city and where we stay when with my brother. The university is worth a walk around, especially to see the hand-painted rocks along the lake shore.

Getting around
Getting around Chicago is easiest by metro and by foot. The metro is a mix of over and underground trains by CTA. It costs $2.50 for one journey, and an extra 25c if you travel twice more (called ‘transfers’) in a 2-hour window. The blocks in Chicago aren’t ridiculously big like in other American cities, so it is definitely worth walking as much as you can to see everything. To give you an idea, we walked from Grant Park in the south of downtown to the John Hancock Centre in the north of downtown and got on the metro at Clarke/Division and that took only 2 hours including photo stops and and some leisurely shopping. Though do wear trainers as I didn’t half moan in my beat-up Vans!

If your feet hurt too much you could rent a bike – a Divvy bike. It’s blue and you’ll find docking stations all around the city. I haven’t used one, but I think they are $3 for 30 minutes or $9 dollars a day, but don’t quote me on that!

I hope this has helped some of you decide whether or not you want to visit Chicago and some possible routes across the city. If you want more specific tips or road markings, comment below and I’ll happily help you out.

We’re heading out of town the next few days so I’ll probably do another post shortly about things to do in the surrounding area. Though I will say one thing, Americans love a toll road!!