This post is in partnership with HotelTonight. All opinions are our own.

Neither of us ever anticipated getting to travel as much as we do. Anddd, no, it’s not like we’re hopping on jets to Bali, or Positano, etc, but even getting to spend a long weekend in a city across the country was, for most of our lives, not something we thought we’d able to do with such ease. Maybe it’s because we’re from a region of the country that doesn’t really prioritize travel? Or that for the first two years of our relationship we were always broke? I don’t know! But I’m so so glad we get to see as much of the world together as we do. Oh my god is this me being grateful? I’m being grateful!

A lot of the travel we do is for work, which is basically trying out a product or service and reviewing / sharing our experience here and on our Instagram. This trip was in partnership with HotelTonight, and if you’ve been around here for a while, you’ve certainly seen other trips we’ve done with them! HotelTonight is a hotel booking platform and here is our 100% honest opinion of why we love it and use it for travel even outside of partnerships with them:

The website and app are both incredibly sleek, simple, and upfront, which makes it so easy to use
They have truly incredible deals and there are many features that allow you to get even lower rates (definitely keep an eye out for their Daily Drop)
Their rewards program (HT Perks) is actually amazing and the more you book the more you can save
They don’t allow just any hotel on their platform, so each hotel you see listed has been vetted by them
They rank the hotels in easy-to-comprehend categories like “basic,” “solid,” “hip,” “luxe,” and “highroller” so you can quickly scan the list of hotels on offer to find what you’re looking for
this is a sample of what you’ll see after you download the app and input a city and dates:

In short, HotelTonight helps make travel more accessible, which is something that’s extremely important to us. We stayed at Thompson Chicago (for a rate of $121/night instead of the original $202/night), which was right near the city center and had all the nice things you expect out of a high end hotel. There was a bar in the lobby with a living wall of plants, many velvet sofas and chairs, a fantastic restaurant, incredible views, and a gorgeous tub situation we were obsessed with. Oh, another travel tip: if you want to have a really amazing hotel experience on a budget, travel off-season. Sure, going to Chicago (or Toronto, Vancouver, Minneapolis, etc) in January is cold but it also means you’ll be able to afford a much nicer spot to stay, and usually you can find much cheaper flights as well. Just a thought!

And, yes, we did leave the hotel eventually. We got literally hundreds of recommendations for things to do around Chicago, which was both so so sweet and also incredibly overwhelming, and we managed to narrow it all down to just a handful of great spots. Our main interest on this trip, to be honest, was to chill out and leisurely explore the city, and we did exactly that. We knew we wouldn’t get to do everything, but that just means we’ll have to come back soon :)

Below are a few of our personal favorites. Please note: this doesn’t include everything we did, and is only like 1/100th of the things there are to do in this city!

The Chicago Athletic Association & Cindy’s Rooftop

The Chicago Athletic Association is 1.) not a gym and 2.) amazing. It’s a hotel / hangout area / bar located right across from Millennium Park, and definitely feels like a throwback to a different, swankier, era. It’s incredibly ornate, with old leather furniture and a gorgeous library and fabulous stairwells etc. The rooftop, Cindy’s Rooftop actually, is amazing (and mostly indoors, in case you’re worried about the weather). It’s got fantastic cocktails, and a view of Millennium Park and Lake Michigan. We cozied up by an outdoor fire and had the best time.

A Day Shopping and Dining in Andersonville

We should probably preface this with: we aren’t people who typically shop on vacation. It’s honestly just not something we consider to be a fun way to spend time. HOWEVER, we got so many recommendations to go to Andersonville and check out the boutiques and vintage shops so we were like OK fine let’s do it. We’re so so so glad we did. Andersonville is a quirky, hip, cozy, and cute neighborhood that has a thriving LGBTQ+ community, and lots of amazing shops and restaurants. Our personal recommendation for how to spend a day here: start by chilling out at La Colombe for a coffee and pastry, then make your way to to Woolly Mammoth for charmingly bizarre antique stuff. Next, walk up N Clark street and hit up the following spots: Brimfield, Scout, Cowboys and Astronauts (you have to go here), Martha Mae, and Roost. For dinner, head to Hopleaf for a wonderfully cozy meal and great beer. If it’s a weekend and you’re up for a show, definitely go see the Neo-futurists “The Infinite Wrench” (more on that right below!). Basically the entire list of stuff to do in Andersonville was recommended by Matthew, the co-owner of Cowboys & Astronauts. He’s amazing, and these recommendations are too!

Neo-futurists “The Infinite Wrench” (Friday & Saturday at 11:30 pm & Sunday at 7:30 pm)

Just gonna say it: this isn’t a huge production, and we mostly happened upon it because Second City (a very popular spot for comedy shows) was sold out and we knew we wanted to see a show. We are SO glad we did, and it ended up being a major highlight of the trip. It’s somewhat grungy, pretty queer, and very crafty. And it’s amazing. The show is a 60-minute production featuring 30 plays that are 2-ish minutes long each, performed by half a dozen or so performers. The plays rotate over the weeks and are written from real life experiences of the performers. Some are hilarious, some are dark, some are interactive with the audience, some are mundane. It’s really, really fantastic. You can get tickets in advance or at the door.

Portillo’s and/or Al’s Beef for Italian Beef

OK so—according to our Instagram messages—Italian beef is a LOADED conversation among Chicagoans. So, please dear god don’t yell at us if you have a favorite place we didn’t include! We didn’t even know what Italian beef was until we started asking for Chicago recommendations, but it’s right up there with Chicago dogs and deep dish pizza when discussing Chicago food favorites. Here’s the 411 in case you don’t know: Italian beef involves French bread, paper thin slices of roast beef, a thin gravy that is basically a French jus, and optional cooked peppers and/or cheese. You can get the sandwich dipped in the gravy, which we highly recommend. It’s a heavily spiced meaty and messy thing from heaven and we are now HUGE fans. We went to Portillo’s and Al’s, though there are like 100 other spots to go for it, and tbh we liked them both so aren’t gonna pick one as the winner. We also had Chicago dogs at Portillo’s, which I think require less explanation (it’s a hot dog with mustard and relish and definitely NOT ketchup and it’s really really really good).

Girl & The Goat and Au Cheval for cute dinner stuff

These two spots got recommended the most for dinner, and with good reason. Girl & The Goat was our favorite, for a pretty simple reason: the food is really great. We typically get weary of super hyped up hip restaurants, but this one delivered. The menu is kind of all over the place geographically (as is the case with pretty much all small plates places) but the prices were reasonable for what it was, and the experience overall was amazing. You’ll definitely want to book your reservation here at least a few days in advance, if not a few weeks.

Au Cheval is actually right next to Girl & The Goat and is an old school dimly lit diner with lots of sandwiches and fries and what not, but they were recommended mostly for their burger. The burger is VERY good. The thing is, though, they don’t take reservations so our wait was 90 minutes, and we were told that was actually pretty short for a weekend. If you aren’t starving, it’s worth the wait. Put your name in and go have drinks down the block at Little Goat, and they’ll text you when your table is ready. If you are super-eat-your-date-hungry, the burger may not be worth the wait to be honest (just our opinion, please don’t yell at us, we love you!!). If you do decide to stick out the wait, you’ll experience an amazing burger in an atmosphere that feels… cool… but not in a pretentious way. You’ll just feel popular and I don’t have any other words to explain what I mean by that.

Boystown

We love gayborhoods, and Boystown is a great one! Don’t let the name get you confused though, there are plenty of spaces for queer women and femmes here as well. Our favorite bars were Roscoe’s and Sidetrack which are both way larger and with more to offer than we’re used to. We watched RuPaul’s Drag Race at Roscoe’s and it was a fantastic experience. Also, along North Halsted St. there are plaques honoring LGBTQ+ leaders and icons, which were great to read during our stroll.

And that was our weekend, thanks for stopping by! Let us know what you think about our time in Chicago in the comments below, and don’t forget to check out HotelTonight for your future travels!

xoxo Beau & Matt

A Cute Few Days in Chicago