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You’ve got to love a city where you can fiercely debate the merits of various pizza styles, go from sand to skyscrapers in moments, and celebrate holidays with such ferocity that you to match it. I’m talking, of course, about Chicago — though I must admit it’s taken me a while to appreciate the city as an adult.

I was lucky to visit Chicago often from junior high, when my cousin Kirsten moved there after college, onward. I visited her once or twice a year, with very little concept of where I was or what I was doing beyond the fact that I was following my very cool older cousin around. I have vague memories of Cubs games and beach days, but it’s all pretty fuzzy.

Chicago Travel Blog

Then I graduated college, and somehow a few years slipped by without me making it out to The Land of Lincoln, though thankfully I saw Kirsten frequently in Martha’s Vineyard, Boston, Belize, and beyond. Last summer, I made it back for the first time in years and I had a blast playing tourist together (blog post still to come since I put 2016 on pause!). I vowed to make it back much more frequently, and Kirsten made that easy for me when she went on and got engaged, putting another wedding on my calendar for summer 2017. Three cheers for back-to-back Illinois weddings!

This particular event turned out to be a very special one for me, because it was the first of the four I attended over the summer that Ian was able to make it to. Fresh from a few weeks of work in Newfoundland, Ian was thrilled to be visiting Chicago for the first time, and I was quite keen to play tour guide after years of being the one led about.

The Freehand Chicago Travel Blog Review

The Freehand Chicago Travel Blog Review

The Freehand Chicago Travel Blog Review

After much debate, Ian and I settled on staying at for the first few nights of our trip. We considered staying at the wedding hotel all the way through (way too pricey), finding an Airbnb (Lollapalooza crowds snapped them up fairly quickly), crashing with Kirsten and Steve (we didn’t want to impose the nights before the wedding!), and The Freehand. When we saw a hotel sale drop fares to lower than we’d seen in our weeks of browsing, we jumped on it.

While Tuesday and Wednesday nights were affordable across the city, Lollapalooza festival made prices skyrocket on that Thursday to nearly double what they’d been prior. We ended up paying $530 for three nights, which despite being in a private room and in a very centrally located area, is quite wince-able for a hostel.

The Freehand Chicago Travel Blog Review

The Freehand Chicago Travel Blog Review

We had mixed feelings about The Freehand. The onsite Cafe Integral was a great spot for breakfast one morning, and you can’t beat The Broken Shaker for a creative cocktail surrounded by hip young beautiful people. There was even a small gym which we used for a workout one evening.

However, compared to their Miami location (which I’ve stayed at) and their Los Angeles location (which I’ve dropped by), there is no pool, which is a major value-adding amenity at the other two. The guest kitchen was very small and dark and while we weren’t in the dorms, the atmosphere was definitely more hotel than hostel — I’m not sure I’d come here hoping to meet other travelers if I was alone.

The Freehand Chicago Travel Blog Review

The Freehand Chicago Travel Blog Review

The Freehand Chicago Travel Blog Review

As for the private rooms, our was truly the smallest I think I have ever stayed in. We actually paid for one level up from the cheapest room — a City View Queen — and when we walked in I thought that they must have made a mistake and put us in one of the cheaper rooms by accident. I do still kind of regret not going and asking if we could be in anything larger, since we did start to feel claustrophobic by our last night, with our bed boxed in on three sides. At least I know really know what under 300 square feet feels like! (Which I’m pretty sure included the bathroom.)

That said, overall, while we weren’t thrilled with our stay, we were pretty pleased. Like I said, the location was great, we love the aesthetics, and it was actually very affordable compared to other Chicago hotels over Lollapalooza period.

The Freehand Chicago Travel Blog Review

The Freehand Chicago Travel Blog Review

The Freehand Chicago Travel Blog Review

Our first evening together, Ian landed late and took a cab straight to Kirsten and Steve’s, where I’d been staying. We had an incredible dinner together at , which I have to really guiltily admit I didn’t take any photos of — let’s just blame my excitement at seeing my boyfriend for the first time in weeks.

Why mention it? Because as you’ll soon see, this trip was the Chicago equivalent of my Where to Get Fat and Drunk in London, and Parson’s was a strong start. But fear not, because Parson’s was good enough that I will be begging Kirsten to bring me back on future trips — and next time, I’ll bring the camera.

North Avenue Beach Chicago

The next morning, after breakfast at Cafe Integral and laptop time in the lobby, we set off for what I humbly consider Chicago’s greatest asset — its urban beaches. Seriously, in how many other cities can you walk from the downtown core and be stripped down to your bikini in less than ten minutes!?

While Oak Street Beach was technically closer to our hotel, we wandered up to North Avenue Beach so Ian could experience the infamous — this really nails the magic of it. We’d been warned it was more of a place to drink than eat, but I quite enjoyed my asian chicken salad and pineapple sorbet. Plus, seriously, can you beat the view?

Castaways Chicago

North Avenue Beach Chicago

Castaways Chicago

Castaways Chicago

Castaways Chicago

Castaways Chicago

After lunch, we got down in the sand! I had to keep reminding both Ian and myself that we weren’t on an ocean — nope, that was Lake Michigan we were dipping our toes into. It was quite the afternoon of sightseeing. In just a few hours, while we sipped subtly on forbidden ciders, we watched a DIY beach baptism, saw a man try to avoid getting his ankle monitor wet, and watched ten thousand tweens pose for snapchat selfies.

The ankle monitor was our favorite mystery — like, um, aren’t those things supposed to keep you at home!? We couldn’t decide if he was just so lucky that North Avenue Beach was within his designated radius, or if he just said, screw it, it’s such a beautiful day, they can come and get me. We liked imagining the latter to be true.

Castaways Chicago

North Avenue Beach Chicago

North Avenue Beach Chicago

North Avenue Beach Chicago

We’d planned to ride Divvy’s back — Chicago’s rideshare program — but we weren’t the only ones who had that idea, and every station we found was empty, even mid-week! So we strolled along the water, ducking into the city at the last moment, instead. It wasn’t a bad Plan B.

Chicago Travel Blog

We had a pretty major evening to prepare for. That night, we’d made reservations at , the cocktail bar by the creators of  Ya know, that Alinea,  in the dang country?

While we haven’t really hit Alinea status yet in life, we did decide that in honor of our third anniversary (um… where did three years go?!) we could splurge for a night at The Aviary. And oh, what a splurge it was! But while I considered weeping and then laughed instead when the $22 Wagyu beef appetizer was delivered — please see it below, if you are able to zoom in enough to see the two dime-sized pieces of meat we received for that price — everything else we tried was so innovative, memorable, and delight-inspiring that it really took the sting off the price tag.

The chefs and mixologists here must have so much fun making this menu. My favorite drink of the night was The Jungle Bird, also pictured below, which has two rums layered on over the other, the top one filled with spherified rum balls that pop in your mouth like little boba tea balls. It’s so good Time Out .

The Aviary Chicago

The Aviary Chicago

When it was time to leave Aviary, we debated stopping for dinner but decided those Wagyu beef bites had really filled us up. Ha! No. We actually decided that after splitting those and two small dessert plates and an impressive number of cocktails — and, ya know, drinking on the beach all afternoon — that what we needed was more cocktails. 

And so we made our way to . Now. I like speakeaseys, and I love tiki bars. Combine the two, and put it around the corner from my hotel? I am all over it. We split the macadamia nut meatballs and the hanali spring rolls, which hit the spot just as perfectly as our rum-based concoctions in ceramic coconuts did. Heads up that this is no hidden gem — the place was rammed on a Wednesday, and we were lucky to get the last table that we did. Plan to wait on the weekends.

After a nightcap back at The Broken Shaker, we were off to bed.

Three Dots and a Dash Chicago

You may not be shocked to hear that we woke up the next morning feeling a tad tender. I knew straight where to go — , which I’d spotted on Google Maps around the corner from The Freehand and knew that I absolutely had to visit, if only to shake the hands of the proprietors and congratulate them on having the greatest name for a donut establishment in the history of time.

But I mean, once I was there, it would be rude not to get a red velvet donut, right?

Glazed and Confused Chicago

We’d been scheduled to go on an architectural kayak tour that day, and I have to say, I was pretty blue that it didn’t work out — it’s the one activity that I’ve been really dying to cross off my Chicago bucket list. However, we were hit with a trifecta of nopes — torrential rain, drinking-induced exhaustion, and my left eye, which I’d just had an ocular MRI for before leaving for Chicago, acting up. Nope, nope, nope.

Instead, we resigned ourselves to a day of eating. Poor us!

Homeslice Chicago

Homeslice Chicago

After a few hours back in bed binge-watching (it’s soooo good, fellow TV-addicts) and in my case, photo-editing, we emerged again to consume carbohydrates — this time at pizza. This venue required a short but super convenient ride on The L, which deposited us practically at the pizza place’s doorstep.

And we got there just in time. Right after I snapped a few photos of the cute airstream in the backyard, another torrent of rain unleashed, and they closed up the back patio. We loved this place — the food was amazing, the location was cute, and we got an excuse to ever-so-briefly leave The Loop for Lincoln Park.

Homeslice Chicago

Homeslice Chicago

After running a few eyeball and wedding related errands, we were back in bed to watch the rain, finish the season and just enjoy a breather in a busy summer. Sometimes you just need one! (Though yes, this was the day we started crawling out of skin in our closet-sized room.)

The next morning, we woke up ready to switch gears into wedding mode. With a large gap between when we could check out of The Freehand and check into the wedding hotel a ten minute drive away, we decided to make brunch reservations somewhere cute. Along with Homeslice, I found the perfect spot via the blog — I met the adorable author Annie at my reader meetup a few months ago in St. Pete, and have been digging her style ever since!

The Hampton Social Chicago

The Hampton Social Chicago

The Hampton Social Chicago

The Hampton Social Chicago

was practically designed for Instagram — I laughed when we walked in and Ian appeared to be the only male in the vicinity that wasn’t on the waitstaff. “Had to peel the plastic off the urinal,” he quipped when returning from the restroom after we’d ordered, surrounded by giggling twenty-somethings drinking rosé.

I adored it.

The Hampton Social Chicago

The Hampton Social Chicago

So, we didn’t exactly do a ton while we were in Chicago. Had the weather been better, I would have loved to have fit in the kayaking tour, or maybe have made a Plan B for a museum visit of some sort. But when life is moving a million miles an hour, I am pretty grateful for a travel buddy who is happy letting me chill on occasion — as long as we’re well-fed and watered, of course.

Chicago Travel Blog

Chicago Travel Blog

Next up: my final wedding of the summer!

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21 Comments...
  • Katie
    September 10 2017

    Wow three years already – congrats Meihoukai and Ian! I love the beaches in Chicago too and when I visited in summer 2013 they were a godsend with 100+ degrees and humidity every day.
    Katie recently posted..

    • Meihoukai
      September 21 2017

      Oh gosh, yes, a beach would indeed be a godsend in that situation! I’d be there every day after work if I was a local!

  • Erin
    September 10 2017

    i HAVE to check out that show now! lol thanks! 🙂

    • Meihoukai
      September 21 2017

      Let me know what you think Erin! TV addict right here ha ha.

      • Erin
        September 22 2017

        Love it!

  • Ijana Loss
    September 11 2017

    1) I have a friend who has to wear an ankle monitor and it allows him to go certain places, but definitely does not include fun places like a beach, so I have no idea what’s up with that guy you saw xD

    2) Geez 3 years already??! It sure did fly by, congratulations to you guys and I hope there are many more years to come!

    3) I would totally go to every place you mentioned in this post and then possibly fall in a food coma and not wake up for a week lmao

    • Meihoukai
      September 22 2017

      … that’s basically what happened to us (with the food coma, ha.) I definitely didn’t do a great job eating healthy in Chicago!

  • Noel
    September 11 2017

    Yay, so glad you made it to Three Dots and a Dash! That was one of my favorite bars we visited when I was in Chicago for the first time last summer. Watershed was another little hidden gem bar that I loved. And for food, next time you are there, I highly recommend Purple Pig (if you haven’t been). Loved Chicago, can’t wait to get back!

    • Meihoukai
      September 22 2017

      Ah, thanks for the tips for next time! With my family nearby, there will definitely be many next times!

  • Annie
    September 12 2017

    We tried so hard to make it to Three Dots and a Dash but the line was so long both nights we tried and it was so cold out so we didn’t wait, it’s definitely on our list for next time! Chicago has one of the best food/drink scenes. Thanks so much for the shout out!

    -Annie
    Annie recently posted..

    • Meihoukai
      September 22 2017

      Man I guess we got lucky — we didn’t wait for a minute! I think we arrived fairly early though and it filled up super quickly after we walked in the door.

  • Dominique
    September 13 2017

    I don’t know much about Chicago, but I do know that if I would ever visit I would eat my way around the city like you did! All the food there looks amazing!
    Dominique recently posted..

    • Meihoukai
      September 22 2017

      Ha, hopefully on my next trip I have more than just food to report 😛

  • jay
    September 13 2017

    Homeslice pizza looks super cute next time I am in chi gotta check that place out !!!
    jay recently posted..

    • Meihoukai
      September 22 2017

      And it was SO tasty. So grateful for that recommendation!

  • Steph
    September 14 2017

    You always seem to find the cutest places to eat and drink. Tell me your secrets!

    Steph x
    Steph recently posted..

  • Leigh
    September 14 2017

    I lived in Chicago in my 20’s and it’s pretty fuzzy 😉 Your visit was the weekend I moved out of Chicago after 12 years, and you can see why I now have 40 pounds to work off 🙁 So much eating to do! Glad you enjoyed your visit!
    Leigh recently posted..

    • Meihoukai
      September 22 2017

      I get it — I think Chicago and New Orleans were my two most gluttonous trips of the summer! TOO much good to eat and drink, ha ha!

  • Victoria @TheBritishBerliner
    September 28 2017

    I’ve never been to Chicago, but I’ve heard that it’s a really cool city, which you’ve just confirmed!

    p.s. Congratulations on your 3 year anniversary with the boyfriend. Nice one!
    Victoria @TheBritishBerliner recently posted..

    • Meihoukai
      September 28 2017

      Thank you — a big milestone indeed!