Chicago City Guide: 48 Hours in the Windy City

Let me preface this Chicago City Guide by saying that we. loved. chicago. I knew I’d like it, but did not realize how much. We basically ate our way through the city, as one does. We fell in love with the many different neighborhoods, the restaurants and bars, and well – everything else.

If you’ve been to Chicago, perhaps you know what I mean. It’s a fantastic city with almost too much to see in one weekend! But, we did it. We saw almost everything we wanted to, which I call a success.

Chicago City Guide: Favorite Spots

We had so many favorite spots that we somehow managed to hit up in the short time we were there. We walked a ton, ate donuts like there was no tomorrow, and indulged almost too much. Okay, actually too much. Hey -it’s vacation, there’s no judgment on vacation. Also calories don’t count. Or carbs.

Where to eat

• Pequod’s Pizza: Yes, of course I need to lead with pizza. It’s Chicago, duh. This spot might not look like anything special, but day-um is it delicious. I didn’t really know what to expect as I’ve never had true Chicago deep dish before. I was slightly against it at first because I prefer thin crust, but when it arrived, I fell in love. And now I want pizza.
• U.B. Dogs: This was one of our first spots. We really needed to satisfy our craving for hot dogs, which I really only ever experience at baseball games. Or, when in Chicago, I suppose. Do yourself a favor and get the Merkt’s Sharp Cheddar. I’m dreaming of it right now. Ugh.
• Summer House Santa Monica: A true escape from the city. The minute you walk in to Summer House, you’re totally transported. It’s filled with natural light, good vibes, and delicious food and cocktails. I can’t imagine this place isn’t packed year-round.
• Au Cheval: When you hear this spot has the “best burger in America” you go. For real. We stopped by late one night and oh. my. gosh. it was incredible. I’d highly recommend it.
• Big Star: This was the only spot we knew we had to try out before we even left Boston. For real. It seriously did not disappoint. The food and drinks were spot on – it really was the best way to kick off our Chicago weekend!
• Chicken Shop: This spot was my favorite. We went on Saturday for lunch, and highly considered going back on Sunday. I’m not even kidding. Yes, even with all of the other restaurants in Chicago that we wanted to try. If you go to Chicago, please visit Chicken Shop. See that burger and chicken sandwich above? Yeah, that should be enough to convince you.
• Stan’s Donuts: Y’all, these donuts were fabulous. There were so many to pick from I was completely overwhelmed. We actually let about 5 people go ahead of us before making our decision. Which donut you start your day with is serious business!

Where to shop

We, admittedly, didn’t do any shopping while in Chicago. It was all about the food, man! So, this Chicago City Guide unfortunately doesn’t include a where to shop section – but if you have any favorites, please share! We already want to visit again, and next time we’ll be sure to shop 😉

Where to hang

• West Loop: We were all about West Loop. After we discovered this neighborhood, we really didn’t want to leave Chicago. In fact, we hadn’t even hopped back on our flight before we were looking up apartments. Sorry, Boston!
• Heritage Bicycles + Heritage Outpost: These spots were the coolest. Delicious coffee (and chai, for me!), unbelievable baked goods, and awesome clientele. At Heritage Bicycles, you can even sit outside around this fire! Nifty, eh?
• Wicker Park: This spot had it going on – lots of bars, restaurants, etc. Oh – and Stan’s Donuts. Boom.
• The Goddess and the Baker: I had the chance to meet one of my long-distance blogger friends for the very first time while we were in Chicago (hi, Emily!) and she suggested this café. It was perfection. We stayed for at least an hour and a half and I didn’t want to leave. The chai was fantastic and the company was even better 🙂

Where to stay

• Soho House ($$$): We weren’t lucky enough to stay at the Soho House (it’s a members-only hotel), but one day – we’re staying there. It has to happen, mainly because I fell in love and now how am I supposed to stay anywhere else in Chicago?
• Sheraton Grand Chicago ($$): There wasn’t anything particularly special about the Sheraton, but that’s where we stayed and we got a heck of a deal. They even upgraded us to a room on the corner (well, it’s a half-circle thing, so there isn’t a corner, but you get it) so we had a view of the river and the city. It was divine waking up to that every morning.

Where to drink

• Lost Lake: A tiki bar tucked away in an unassuming building. It was the best escape from the cold, rainy day we were experiencing outside. This place was the best. The owner, Paul, ended up being our bartender and he was phenomenal! So welcoming and also, makes a kick-ass tiki cocktail. Just sayin’.
• The Aviary: Our friend Cynthia suggested this spot so we met up with her there. Thank goodness she clued us in on its concept – entirely experimental. The cocktails were damn good, but pricey. #worthit
• Maude’s Liquor Bar: This was a suggestion from the oh so kind Danielle – I’m SO glad we stopped by! I grabbed a whiskey drink and oh man, A+.
• Corridor Brewery & Provisions: If you’re looking for a classy brewery, this is it. We visited a few while we were there, but this was by far, my favorite. It was an adorable spot with great service, good food (the pretzel was delish!), and of course – tasty beer.

I can’t end my Chicago City Guide without seriously thanking everyone who gave us recommendations. Cynthia – Aviary and Summer House Santa Monica were spot on, and the burger at Au Cheval was bomb. Danielle – Maude’s was a dream! So happy you suggested it! I know I’m neglecting to mention so many of you, but thank you all so much for your suggestions! We wish we could have gone everywhere. Well, yet another excuse to head back.

What’s up next on your travel list?

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