Spending 36 Hours in Chicago, Illinois.

We began our big American roadtrip in Chicago over the St Patrick’s Day Weekend, and with just one full day to explore the city, it was a race-against-time to see as much as possible and more importantly, EAT as much as possible!

Thankfully we found Chicago was a really chilled out and laid-back city, with everything very close-by, so we pretty much conquered the main tourist sights of the city that we were interested in seeing (and its food) in our one-day allocated.

I absolutely fell in love with the city though, and am now desperate to go back for a long weekend to really experience it properly! If you’re short on time like we were though, or just keen to see a glimpse of what the city has to offer, keep on readin’.

Ready to find out how to see the most of Chicago in 36 hours? Let’s go!

We arrived late in the afternoon on Saturday once the St Paddy’s Day Parade had finished (for some reason they always hold it the Saturday before St Paddy’s Day, even though the day itself was on a Sunday this year), and after a very early start (hello, 3am alarm clocks), and long non-direct flight, we were exhausted.

We decided to spend a couple of hours in the hotel spa to rest before the busy day we had planned the next day, and after being in total AWE at the bright green river that had been dyed for St Patrick’s Day, we got changed and napped in the sauna and steam rooms of the hotel.

That evening we just went for dinner at Cheesecake Factory – it’s located right up Magnificent Mile which is about a half hour walk from the hotel so it was a good excuse for us to stretch our legs, and we really wanted a proper ‘American’ experience for our first meal (also, Cheesecake).

 

See the famous Chicago Theatre

The next morning we woke up bright and early (thanks jetlag!), and hit the streets of Chicago for our day exploring the city. We were staying in the Langham Hotel which is right on the banks of the Chicago River, and it was super easy to get everywhere from there. We crossed over the bridge, ogled at the river some more, and then walked over to the Chicago Theatre for some snaps.

 

Cupcakes and banana pudding from Magnolia Bakery

Our next stop was Magnolia Bakery. I know this is a New York thing and not a Chicago thing, but I love their cupcakes and banana pudding SO MUCH, I was desperate for them. And I haven’t had them since my last NYC trip over a year ago! So I obviously treated myself and it was absolute heaven. After Magnolia Bakery we wandered down the street and then across towards Cloud Gate and The Bean!

 

Take photos with The Bean

This is probably Chicago’s most famous sculpture, and we absolutely loved it! We were crazy lucky with the weather and our beautiful blue-sky day allowed for the best photos and glimpse of the city. The Bean looked so beautiful in the sunlight, and I was totally mesmerised by it.

 

See an old-fashioned L-Train

We then took a wander around the park, and then headed up towards Uno’s Pizzeria for an early lunch. On the way we saw an L-Train rattling by overhead, and I was MESMERISED. I absolutely love the train tracks above the road and it was such a novelty to see a train travel over us!

Deep dish pizza from Uni’s Pizzeria

We’d heard about the insane queues at Uno’s because it’s one of the most famous places for Deep Dish Pizza, and also that the pizza can take up to 45mins to cook because it’s all made fresh, so we decided to get there for 11:30 so we could eat by around 12:15/12:30.

This worked out PERFECTLY, and I highly recommend doing this! There was no queue for the restaurant, we were served quickly, and our pizza arrived bang on 12:15!

 

The pizza itself was amazing. Oh my days. The pastry was like sweet shortcrust pastry and was all buttery, and the fillings tasted SO GOOD. Deep Dish Pizza is basically like a pie, and we found that sharing a ‘Small’ pizza was enough for us, as it meant we had two slices each.

After those two slices we were completely full and it kept us going for a few hours! You can see above just how painfully full I was after my two slices, haha…

After Uno’s we walked up to the Magnificent Mile which is the main shopping street. We didn’t really hang around here as we didn’t really want to waste any time on shopping, so we just crossed across the street and towards Navy Pier.

Navy Pier is super cute to walk around and look back at the city skyline. I absolutely love the water and being close to it, so for me this was one of my favourite parts of Chicago. Lake Michigan is so beautiful and it looks like the ocean because you can’t see the other side of the lake it’s so big!

Visit the American Writers Museum

After wandering up and down Navy Pier we headed over another bridge and back to the city, and walked to the American Writers Museum. It’s a really small museum but worth visiting, with a really interesting exhibition on the most popular American Writers.

After all our walking we were in need of a sugar-boost, so headed back to Magnolia Bakery for their delish Banana Pudding (plz don’t judge us! We did share a small one haha), and then up to the Union League Club to have a nosey as I’m a reciprocal member through my London private members club.

En-route we spotted the famous Berghoff’s bar, which is one of the oldest bars in the city, but is unfortunately closed on Sundays.

We did a little bit of shopping on the main street, and then headed back to our hotel for a little rest. After a bit of chill-out time in the club lounge, we got changed and headed to the original Billy Goat Tavern on Michigan Ave for a burger!

‘Cheezborger’ dinner at Billy Goat’s Tavern

Billy Goat’s is one of Chicago’s most famous bars and burger joints, is a favourite of Chicago-native Bill Murray, and has been open since 1934. The burger is very simple with just a patty, cheese, onions, sauce, and bun, but it was so good and just what we needed after our day of walking over 25,000 steps!

After our ‘Cheezborger’ we walked over to Three Dots and a Dash, which is one of the hottest bars in Chicago right now.

Cocktails at Three Dots and a Dash

It’s a Tiki bar and feels very similar to Mahiki in London. We had a cocktail each and then tiredness and jetlag got the better of us, so we retreated back to the hotel to get a good sleep before our long drive down Route 66 the next day!