A Guide to the Windy City:

Over the last year and a half, Colin and I have visited Chicago four times (full disclosure, several of these have been Sandlot related). For two people who enjoy exploring new cities, it really says a lot about Chicago that we love it enough to be repeat tourists as often as we are! If you followed our anniversary trip on IG, you know that Colin surprised me with a quick overnight here recently. I’m going to outline exactly what we did on our most recent trip, and throw in a few other places that I highly recommend.

Where we stayed:

The LondonHouse: I’ve actually written about LondonHouse in a previous blog where I outlined how we used our Hilton Points to travel cheaply, but I thought I should take a second to talk about it a little more in-depth.

We absolutely LOVE LondonHouse. People are often surprised by how inexpensive it is in comparison to other Chicago hotels that have a lot less to offer. LondonHouse is right off of the Magnificient Mile and is actually located on one of the main canals in Chicago. The location is great because it’s within walking distance to many different restaurants, shopping spaces, and The L (AKA The Loop - which is Chicago’s public transportation rail).

One of the best features of LondonHouse however is their rooftop patio. I’m not sure there’s another rooftop in all of Chicago that boasts a view quite like LondonHouse. Usually (read, not during COVID) the rooftop is easy to get into, but in light of everything going on, reservations are 100000% required, and pretty far in advance.

We booked the hotel using Hilton Honors points, apply for a Hilton Honors Credit care here to get bonus points.

Where to eat: (honestly, where do I even begin)

Sienna Tavern: As a self-proclaimed pasta aficionado, this place is a must. Order the pesto gnocchi, and don’t look back. (This is hand’s down my favorite place for food in Chicago - so much so that in 2019, Colin flew us to Chicago for a last-minute date night just because I LOVE SIENNA TAVERN)

Gilt Bar: With low lighting and a slightly more expensive menu, Gilt Bar is the date spot. They also have a photo booth in the basement that is perfect if you’re looking for a less traditional option for a souvenir from your trip! (P.S. - I order the gnocchi here too. Ya girl loves some potato pasta okay lol)

Beatnik West: There are several Beatnik locations in Chicago, but West has the best aesthetic. As far as the atmosphere goes, it’s untouchable. The Mediterranean + Spanish + American fusion creates a globe-trotter feel as you settle amongst the palm branches and on to thick embroidered cushions. I’d argue that this is one of those places that you go to more for the atmosphere than the food, but make a reservation nonetheless! 

The Hampton Social: As the name suggests, Hampton Social is nautically themed as it imitates the swanky vacation destination along the coast of Long Island. Their fare includes lobster rolls, summery fruit salads, and serves rose all day (and has a giant neon sign that claims as much) and honestly, it is a whole dang fancy beach house vibe. 10/10

Spiaggia: Spiaggo is where Colin and I had our anniversary dinner. While the food and views were fantastic, it’s probably a space for a slightly older crowd. Very classy, and very expensive. (I’m not saying don’t go, but I am saying be sure to consider that before making reservations!)

Barrio: This is for those of us who love Mexican food, even on vacation. Barrio is rustic + industrial + trendy, all perfectly packaged with a tequila menu that will rival Guadalajara. Also, GREAT patio.

A quick note, during COVID reservations are a must. Restaurant capacities are limited and so it’s important to make a reservation to ensure you get a table.What to do:

Second City: An improv comedy enterprise where you can watch a 2-hour comedy sketch that will make you belly laugh. Fun Fact: This is were Amy Pohler got her start!

The Skydeck at Willis (Sears) Tower: Not for the faint of heart (I sat on my butt and scooted our because I am absolutely terrified of heights. However, Colin loved it. And apparently so did the girl before because she was doing cartwheels and handstands like she had something to prove. The Skydeck definitely has the best view of the city, if you’re not afraid to stand in a glass box on the 103rd floor.

Millennium Park (The Bean): Yes, I know this is a tourist destination. No, I don’t care. It’s still cool. 

Magnificent Mile: Upscale shopping and luxe fashion brands because a little window shopping never hurt anyone. Plus, even just walking up and down it is fun.

Chicago Crime Tour: Do you like mob history and getting a tour of their old stomping ground? This is for you. Honestly, it is so fun and educational. Our tour guide did a FANTASTIC job holding your attention span.

A quick closing thought: If you’re flying form KC, check the low fare schedule on Southwest’s website! There are often round trip tickets for less than $100. 

I thinkkkkk that’s it. Honestly, I love Chicago so much that I could write a dissertation on it. But alas, ain’t nobody got time to read that when looking for simple travel recs.

Feel free to reach out if you have any questions!

xx