10 things to do with 48 hours in Chicago 

Living in the UK, most of my travels tend to be in Europe – it’s so easy to hop across the channel for a long weekend and within a few hours you have such a variety of different cultures, languages, histories, cuisines, activities… But when James was offered a job at the university of Notre Dame, a few hours outside of Chicago, I knew I would be on several flights across the Atlantic over the next few years!

By the time he left, at the beginning of August, I already had my flights booked for a long weekend in September. And with iMessage and Facetime the weeks flew by until it was time for me to head the airport!

I had four nights in the US and we’d decided to spend 2 in Chicago and 2 in South Bend. I’ll write about South Bend later but here’s what we got up to in Chicago – this was just my first trip so clearly I am sure I missed out on a lot of great stuff! I will be going again so please do tell me everything I have missed 🙂

My plane landed at 6.30 into O’Hare airport. I am always surprised about American airports. For a country at the forefront of technology and innovation in so many ways, your airports are so outdated and rubbish! We complain about our runway space in the UK but at least our airports are shiny and efficient. I had to wait so long for my bag to arrive (no wonder Americans love taking carry-ons) but then easily jumped in a taxi for a quick ride to my hotel – less than $40 and it only took about half an hour. James was waiting for me in the lobby, we dropped my bag off in our hotel room then swiftly headed out for dinner. We had loads of great meals in Chicago so they will form a blog post all on their own. Jetlag then hit so I didn’t get started exploring Chicago until the next day.

Here’s what we got up to.

1. Buy a bike 

Okay – this might not be the standard thing to do when you visit a new city. But I wanted to include this briefly as a shout-out to a brilliant bike store – Johnny Sprockets. If you are a cyclist in Chicago you will LOVE this store. James was looking for a bike to see him through an Indiana winter and we have vague dreams of bike touring – he got chatting to the shop owner who spent over 2 hours with James talking him through the various options. James wanted a bike with the same geometry as his Genesis back home – a make not found in the US – so they went on the website together and spent ages doing calculations and comparisons. It really was brilliant service. While all of this was going on I was drooling over new bike shoes, jerseys,  jackets, bibs, gloves, lights, locks, saddle bags…. Not being in the market for a new bike myself I was all over the accessories!

James came away having ordered a lovely new bike to be delivered to his home in South Bend, thoroughly pleased with the service.

2. Walk along the lakefront 


Chicago is home to 18 miles of trail running alongside Lake Michigan – a runners dream. Although, despite the bike paths, perhaps not a cyclists dream as these spaces are always filled with people and casual riders so not best if you want to go fast on a nice bike!


We headed to the path our first morning in the city to make our way up to Johnny Sprockets, walking north along the path for almost an hour, gazing out at the boats sailing on the lake, turning around to admire the Chicagoan (is that right?!) skyline, admiring the runners that went past and watching the fishermen.


We also walked past North Avenue beach – deserted in the early morning slight drizzle – but huge and I could well imagine how busy it would be on a hot summer’s day! What a fantastic place to have right in the middle of a city.

The next morning, I went for a run along the same lakefront path but this time in the opposite direction – south, into the city. It was an awful run for a number of reasons which I’ve already written about but one thing that was not awful was the route. It was just glorious. There were SO many runners and cyclists out, I felt like part of a huge community. I also noticed a lot of open water swimmers in the lake, and there was a specific section of beach that even had lockers for swimmers to leave their stuff in.


Being a triathlete in Chicago must be so easy! Oh wait – except for those ridiculously cold winters and horrendously hot summers.

Anyway – the lakefront path is a fantastic resource.

3. The Art Institute

You can’t visit Chicago and not visit the Art Institute. Unless you hate art I suppose. I thought it was wonderful – such a huge array of different types of art, from Greek and Roman busts to the impressionists, to modern art. There was a special exhibition on America in the 1930s which I particularly enjoyed – I have always loved Hopper. You could spend days in this gallery – there are over 300,000 works of art after all – but we didn’t have days so we looked at the map, figured out what we were particularly interested in and then headed that way. The art gallery is really very easy to navigate for a building of its size – there is free wifi in the building which you can use to download the Art Institute map. This interactive guide will then show you where you are and what the art is in that particular room, along with an audio guide to some of the paintings. There is really no need to pay for a traditional audioguide! I wish more museums did this.


4. Millennium Park

After the Art Institute we went back outside to explore Millennium Park with the famous “bean”. It’s actually called the “Cloud Gate” and it’s a sculpture by Anish Kapoor – the incredible reflections showing a distorted version of the Chicago skyline and the faces of lots of tourists posing for that obligatory selfie – said tourists including James and myself of course!


We then continued wandering through the park – it’s beautiful, quiet paths and lovely flowers with so many random art installations dotted around.


5. Wander around the Loop

This is the Chicago business district, called the Loop because of the elevated train lines that runs above the road in a loop. It’s one of the areas in Chicago (if not in the world) with the most striking architecture (more on architecture later!). There are so many incredible buildings, there is the river and the public paths and restaurants that run alongside it, it’s also the cultural theatre centre of Chicago. It is touristy – you can’t escape that – but at the same time it is filled with busy-looking people in suits scurrying to and from their incredible buildings.

We walked through the Loop from Millennium Park to get to our lunch spot –  Revival Food Hall. If you like food, you must have lunch here when in Chicago. It’s quite new, only opening this summer, and is an indoor food hall on the ground floor of one of those huge office buildings. It’s filled with different stalls serving quick, tasty and cheap meals for a great lunch on the go – important when you only have a short time in the city!


6. Go shopping 

On our last morning in the city we wandered from our hotel in the Gold Coast area of Chicago down North Michigan Avenue towards the centre of town. This street is referred to as the “magnificent mile” and it is lined with beautiful buildings, from the old to the new. These buildings are also now filled with so many shops so I stocked up on some staples in J Crew and then we played with iPad Pros in the Apple store and I drooled over trainers in Nike.

7. Take the architectural boat tour

As we walked down North Michigan Avenue, we came to the Chicago river. We had been weighing up whether or not we would have time for an architentural boat tour but as we reached the river, I saw the stall for the tour and we found out a boat was leaving in 1 minute. Perfect timing! We bought our tickets and rushed down to the boat.

I would really recommend doing this tour. From the river, you get a much better view of the buildings than you get when you are in the Loop just staring up at them, you can really appreciate the architecture. Our guide was really enthusiastic and knowledgeable – not only does the boat tour teach you about architecture, it also taught us a lot generally about the history of Chicago. It took about an hour and a half, there’s a bar on board and I just really enjoyed seeing the city from a different angle.


8. Eat a hot dog

Chicago is famous for its hot dogs. And hot dogs are my favourite food. Match made in heaven. There are numerous hot dog stands all over the city but we decided to go for a posh one – the hot dog at Allium in the Four Seasons hotel.If you want something a bit more relaxed and traditional I’ve heard Portillo’s in River North is pretty good.


And finally – 2 things we didn’t manage due to my jetlag but that I want to make sure we do next time……

9. Go up to one of the viewing platforms or have a drink at the Signature Lounge

Viewing platforms on the top of high buildings can sometimes be slightly underwhelming – especially given they are often very expensive these days. In Chicago, you can head to the skydeck at the Willis Tower or to the observation deck at the 360 building. I’m tempted by the Willis Tower as it has glass ledges where you can stand and stare down at the city beneath your feet. Sounds terrifying but fun at the same time! On the other hand, the 360 building has a bar, the Signature Lounge, on the 96th floor. Drinks aren’t cheap but they’re not ridiculously extortionate so maybe I’ll just head there for a drink instead.

10. Go to a jazz club 

Chicago is one of the jazz capitals of the world and I love jazz bars. I had a wonderful time in a jazz bar in New York last time I was there. SoI was really keen to see some jazz. But I was so jetlagged, my second night, by 8.30pm I was so tired I could barely keep my eyes open. Staying awake to go to a jazz club was just not going to happen. So next time I have to plan my trip slightly better, go to South Bend first and spend some time in Chicago when I’m less jetlagged! If you have any recommendations as to which jazz club I should go to, please let me know!

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5 comments

  1. I really didn’t like Chicago, though I visited in January. Holy God was it cold. The over-priced life just isn’t for me. All I can think, no matter how good the food or view, is “what a colossal waste”.

    • It’s all relative – I live in London so other than one over-priced meal which we didn’t love, everything seemed pretty reasonable to me! I’ve told James I’m not visiting him in the winter though, he’ll have to come home to the UK 🙂

      • I don’t blame you for not coming here in the winter (December and January aren’t too bad. The worst is February. You don’t want to be anywhere near here in February (I’m only 3-1/2 hours from Chicago, north of Detroit in Michigan).

        The “overpriced” part had to deal with the price of the hotel I stayed at. Now, this was a business trip, so I didn’t pay a dime, but the room I stayed in was a few hundred bucks for a night (stayed two or three blocks from the water). This was maybe fifteen years ago now… Anyway, I learned that not only did they have to pay four times what I would pay for a room here at home, they wanted another $65 to park a vehicle. Just seemed ridiculous.

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