Every May, me and most of my moms decide to escape reality for a very short time and head to the big Windy city for a day or two. It’s kind of, sort of a Mother’s Day trip with three out of the four most important moms in my life. (My momma, my Carrot momma and my Carrot grand momma. My own lovely grand momma happened to be busy this particular May).

We eat and we drink and we play and we walk and we visit parks and bask in the sunshine and drink too much coffee. Sometimes we shop on Michigan Avenue and pretend we have more money than we actually do and go into stores that would mortify our husbands if we showed them just one price tag. Sometimes we hit up museums because Chicago has incredible museums. Or sometimes (like this year) we save all our museum admission money for a very nice room in a very nice hotel with a very nice rooftop bar. Rooftop bar or museum? I know, it’s a hard choice.

Also, if you ever get the chance to take a little trip to a big city with an 80-something year old woman, I highly recommend it. You will make friends everywhere you go. People will always be nice to you. No one will care how poorly you are at ordering in trendy places. Everyone will smile. And you will see the big city through their excited, can’t-believe-how-big-and-fast-this-world-has-gotten eyes and you will appreciate it all, all the more.

Here’s all the sights and eats and drinks of our lovely 26-hour getaway:

Nookies Too // This cute little place was our official first stop after looking in the windows of about a million places that did not serve lunch on Thursday. Rude. My first choice was Cafe Ba-Ba-Reeba but it too was closed so instead we happily found a seat in this calm, fresh, homey little breakfast and lunch place then shared a salad with chicken, red peppers, feta, grapes and balsamic, some bomb ass split pea soup (if you ever thought there could be such a thing) and a turkey reuben.

Toast // Rounded the corner only to see this breakfast gem. Too little, too late. But shucks, I do love me some toast. Next time I am taking my Carrot here for sure.

Mrs. Greens Natural Market // We stopped in a cute little natural grocery store on the way to Lincoln Park for some very unhealthy treats. The french toast cake ball might have changed my life. I could eat a lot of these things. If I lived in Chicago I’d no doubt stop at this cute little place for healthy things instead, but it was a 26-hour foodventure. No health items allowed.

Lincoln Park // Number one, it’s free. Number two, it’s beautiful. Number three, it’s got killer views of the city. Number four, it’s free. Number five, it’s close to the cutest neighborhood. Number six, I easily found street parking. And um, did I mention it’s not only free but it also has a free zoo?!

Millennium Park // If you don’t know about the Bean, well then you better get your ass (is that the second time I said ass in one post?! Forgive me. I get worked up when I’m talking about cool places) to Millennium park. Stat. Maybe try for a summer Wednesday and listen to some free music too.

Chicago Cultural Center // No admission. Usually some quirky cool art exhibit. Oh and it’s an old public library with a third floor so breathtaking you can’t even believe it with about a dozen or more mosaics dedicated to a love of books, literature and words. Hands down my favorite semi-hidden gem in the whole city.

Elephant & Castle // This place. Oh, this place. It. totally. rocks. We were looking for a place to park our tired-from-walking butts before taking my mom to the train station to catch her train home. We wanted some snacks, some good, strong beverages and a patio where we could linger. We chose this cute little chain restaurant with pub food. We had low expectations. We got much more. Our waiter was the most adorable human to ever walk the planet. Funny, accommodating and completely relaxed, he reminded me how much I love good, friendly service. Spicy Bloody Marys, deep-fried pickles, garlic pretzel breadsticks (what?!), a turkey club wrap and this thing called the Slum Dog (that really really messy hotdog wrapped in paper) which may have been one of the most delicious things I’ve ever eaten in my life.

MileNorth Hotel // This hotel has a rooftop bar. A bar on the rooftop. You can have as many drinks as you want on the rooftop and then stumble back into your room only a couple floors away (not that that’s what we’d ever do….) all while looking out at the beautiful skyline of Chicago. ON THE ROOFTOP. According to my fancy Chicago friends this isn’t that extraordinary, this whole rooftop drinking thing, but it was my first time drinking an Old Fashioned with that kind of a view so I’m just gonna keep on raving. The hotel also has an adorable coffee shop in their massive lobby. And everyone who worked there was smiley and accommodating and acted like they didn’t even know we were just a bunch of country bumpkins. I loved them and this place and obviously the rooftop bar. I will be back.

Firecakes Donuts // I’m not sure why Chicago and fancy artisan donuts go hand in hand in my mind, but for some reason or another they do, and I was absolutely obsessed with the idea of savoring dozens of creatively-flavored, mounth-wateringly delicious donuts for breakfast on our trip. It might have had something to do with why I wanted to spend the night in the first place. Shhhhh. Don’t tell. Donut addiction is real. We devoured many fillings, frostings and flavors. There was no clear winner. The plain ol’ Vanilla Iced was like a giant (and I mean giant) Krispy Kreme covered in soft, decadent white frosting and pretty little sugared pearls. It was obviously spectacular. The Maple Glazed Pineapple Bacon and Butterscotch Praline joined the Vanilla Iced in the running for best damn donuts I’ve ever had.

Michigan Ave // Yes, I only let myself go into one store (Zara) and yes, I still spent $100. That’s why I only let myself go in one store. We were so restrained.

Gino’s East // Personally, I’m partial to Uno’s or maybe even Giordano’s but Gino’s East was smack dab beside our killer hotel and it was a last minute can-we-fit-in-some-pizza-before-we-leave kind of decision and the pizza may not be my very first choice (shhhh) but the ambiance and accommodatingly wonderful staff more than made up for it.

With all my Chicago love,
your Leek