How to Spend a Long Weekend in Chicago - Part 2

18 December 2019

Following on from my first post about our long weekend in Chicago, I thought I better get 'part two' up pretty sharpish! If you missed part one, you can read it here.


On Sunday we were still up bright and early {thanks to the Zara delivery man who called me all the way from the UK at 4am US time 😅} but after Saturday night, we opted for a slow morning and made our way across town to the highly recommended Little Goat Diner. We'd booked a table and if you're planning a visit, I highly recommend you do - it was packed, and for a good reason. The food was divine...we started with a Cinnabon as big as my head {God bless America!} and even as someone who hates cinnamon, I loved it. Followed up by a spanish omelette for me with a side of hash browns big enough to feed a small village, french toast with fried chicken and an asian breakfast bowl for my friends. We all thoroughly enjoyed our food and would have definitely gone back had we found it earlier in the trip 🤤. We also stopped by their Photo Booth on the way out which I think is such a cute idea, I love printed photos and definitely don't take enough of them!

After we were suitably stuffed, we headed back to the Loop to start our Chicago Crime and Gangster Tour. I'm not normally one for organised 'tourist' tours, preferring to just wander around when and where I want to, but this is one of the tours I fully recommend you take part in. If you're at all interested in crime, 20s/30s gangster culture or just love a murder documentary..then this one's for you. We booked our tickets through Get Your Guide for around £30, and it was well worth the money. Our guide was funny, engaging and full of information...and I even managed to get myself pushed into a mobsters secret underground safe {blurry photographic evidence below!} 🙃. 

After we'd all finished gushing about how great the crime tour was, we headed to London House for a glass of wine with a view. The inside of London House is lovely, but the magic lies in the terrace outside, with an unbeatable view of the river. Again, I'd imagine is better on a summer's evening when it's not freezing and misty, but it still had its charm on a foggy December afternoon. Definitely not a spot to miss if you're a fan of a drink with a view! They also pride themselves on being a great place to propose if you're planning to pop the question in the windy city! 

After London House, we took a short wander down to the Chicago Theatre to get that classic tourist shot once the sun had gone down and you could really see the lights in all of their glory, before heading back to the hotel to get ready for dinner. Sunday night meant it was finally time for us to go our for some traditional Chicago Deep Dish Pizza and we were so excited. We'd spent the entire trip asking every Chicago native that we bumped into where we should go for pizza and got a different answer pretty much every time...the two that kept coming up were Lou Minati's and Giordano's, and in the end Lou Malnati's won out 🍕. We went for their classic cheese and sausage deep dish pizza and it did not disappoint {we shared a medium between 3 of us and it was plenty of food!}. I never got time {or the room in my stomach} to get down to Giordano's but I'm told if you want a more cheesy pizza then it's the place to go, and if you want a more saucy pizza then Lou Malnati's is for you! 

After pizza we headed to the Library at the Gilt Bar, a hidden speakeasy, for French and Dirty Martinis to finish the night. We were still quite tired and jet lagged so didn't stay long but the bar had a really cool atmosphere and a vintage Photo Booth where you can get your photo taken {for free} and stick the spare strip of photos on the wall with the date you were there - a very cool idea, and it was really fun to see everyones photos up on the wall! 


Monday was our final day in the city, and lucky for us our flight was late in the evening so we had the whole day left to enjoy the city. For brunch, we headed to 3 Arts Club Cafe which is a beautiful 'outside on the inside' themed cafe in a Restoration Hardware {worth going just to have a look around the shop - it's stunning!}. I had a truffle grilled cheese which, although isn't your typical brunch food, was incredible. 

After brunch we walked down to the 'Magnificent Mile' for some shopping...aka, spending all of my money in Sephora and took a little lunchtime visit to the worlds biggest Starbucks. It has 5 floors, a bar and a roof terrace! I wouldn't say you *need* to see this, but if you find yourself walking past and there's no queue then why not pop inside...if you actually want a coffee, there's a regular Starbucks across the road with no queue 😅. 

After we were thoroughly shopped out, we headed to Barrio for a mexican dinner before our flight. If you like mexican food, then I can't recommend Barrio enough, and they also do an excellent margarita {on happy hour if you head there early!}. We started off with these epic nachos and then I went for the Mahi Mahi tacos which were one of the specials that day, I'd definitely recommend them if you see them on the menu again!

As you can probably tell by all of the gushing, Chicago was amazing - somewhere I'd recommend anyone to visit. The city has so much history, but is also awash with modern bars, restaurants {with some of the best food I've ever eaten}, the loveliest people and plenty to do! I'll definitely be visiting again one day - although maybe in the summer where thermals and 3 pairs of socks aren't such a necessity! 

xo Becky 

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