What to Do in Chicago: Weekend City Guide

I recently surprised my mama (fun fact: she’s also my photographer and “momager”) with a weekend trip to Chicago. She had just finished her second Master’s after spending the past NINE years in school (while also having a full time job, being a full time mom, and oh yeah…she works out every day. #Boss), and it was high time to celebrate her success. So, we packed out bags and jetted off to the Windy City for a weekend! This was my third time in the city, and my mom’s first, so we hit a bunch of typical touristy spots while leaving room for spontaneity along the way.

We had a BLAST and jammed so much in while still feeling refreshed and relaxed. If you’re planning a trip to Chi-Town or if you’re just curious to see what to do in Chicago, I’m rounding up what I’d consider to be the best option to add to the agenda if you’ve got a weekend in Chicago coming up!

 

Day 1:

Chicago River Boat Tour. We did the most popular option – the Chicago First Lady Architectural boat tour. Hands down the BEST way to see the city and get the city’s story right off the bat. I think Chicago’s skyline is one of the prettiest around – everything just glistens! – and knowing the history behind historic buildings and fun facts of each neighborhood is a fabulous way to get acquainted and get familiarized ASAP. TIP: If you’re going in fall/winter, wear a coat! It’s a weeeee bit chilly on the water. My blanket scarf kept me quasi-warm, but holy moly, Chicago is cold.

What to Do in Chicago: Weekend City Guide

What to Do in Chicago: Weekend City Guide

Virgin Hotels Chicago. Virgin’s first hotel is in Chi-Town, and I had the opportunity to stay with them during our girls’ weekend. Y’all…it was epic. This place is SO fun. Accommodations are beautiful; the rooms (specifically, any washing/bathing areas) were actually designed with females in mind, so everything from benches for shaving to a fully-illuminated ring lit mirror are there so you’re taken care of in a home-away-from-home feel. We spent probably way too much time at Miss Ricky’s – the hotel diner-esque restaurant. Chef Rebecca (who was on Top Chef, nbd) made a hand-picked selection of goodies for us to taste on Thursday night, and we enjoyed brunch on Saturday there, too. She is beyond talented, and honestly it’s an honor to eat what she makes – everything feels like it was craft fully, tastefully made just for you. The hotel has so much to do, from the second floor lounge and bar called The Commons Club (ask for the Lady in Red!) to rooftop concerts, so it’s truly an experience and not just a stay.

What to do in Chicago: Weekend City Guide on Coming Up Roses

Day 2:

Lincoln Park Zoo. Hands down, the highlight of our trip. I had never been before, and I had no clue that this total gem of a zoo is completely FREE. Mindblowingly good. If you follow me on Snapchatย (erica_lig), you might’ve caught the zoo antics…as in an entire family of gorillas playing together, a giant tiger who wanted to befriend the humans, and kangaroos AND tortoises feelin’ the love, if ya catch mah drift. ๐Ÿ˜‰ Our trip was educational and hysterical, and five hours later we had spent the whole day with the animals.

What to Do in Chicago: Weekend City Guide

What to Do in Chicago: Weekend City Guide

Lincoln Park Conservatory. Located a hop, jump, and skip down the sidewalk from the zoo, the conservatory was such a cool hidden gem to check out. I swear every plant you could ever think of was here, including a sausage plant. Yes, sausages grow on trees. Apparently. HA.

What to Do in Chicago: Weekend City Guide

What to Do in Chicago: Weekend City Guide

What to Do in Chicago: Weekend City Guide

What to Do in Chicago: Weekend City Guide

What to Do in Chicago: Weekend City Guide

What to Do in Chicago: Weekend City Guide

The Magnificent Mile. Chicago’s highlighted shopping district. If you’re up for emptying your bank account, brace yo’self – it’ll happen here. We didn’t go for the shopping spree, but just to check out the culture of it all; we ended up stumbling upon the most fun street performer ever, who was jamming out on his saxophone like a total beast.

 

Day 3:

Brunch at Miss Ricky’s. Miss Ricky’s brunch is the bomb dot com. Chef Rebecca’s avocado toast is UNREAL, and their menu is super specifically curated; some fan favorites are chicken and waffles and biscuits n’ gravy (which I had, and holy foodgasm).

What to do in Chicago: A Weekend City Guide

The Bean/Millennium Park. A total tourist staple amiright?? This is a *must* on your “What to do in Chicago” list. The Bean is that giant silver, welp, BEAN located in Millennium Park. I lovelovelove Millennium Park in summertime, because there’s always fun little concerts and events happening outside. In winter, I’m more likely to be found warming up in the Starbucks across the street. ๐Ÿ˜‰

What to do in Chicago: Weekend City Guide on Coming Up Roses

Upside Down Tea Party. From 2-5 on Saturday’s and Sunday’s, Virgin does an Upside Down Tea Party. And lemme tell ya…this ain’t the Queen’s tea and crumpets. ๐Ÿ˜‰ Boozy tea concoctions + the most ABSURD dessert sampler are served to all, and you leave feeling all of the above.

What to do in Chicago: A Weekend City Guide

What to do in Chicago: A Weekend City Guide

What to do in Chicago: A Weekend City Guide

The Willis Tower. I mean, it’s the tallest building in the country (still in my book, since the new World Trade Center has a massive spire that knocked Willis down from its title). The observation deck is a must, especially the glass landings where you can step out and see the entire city below, from 104 stories up! We went around sunset, which was AMAZING – seeing the lights for miles was truly unreal. And someone got engaged on the clear deck right in front of us. IDK if I’d want to be proposed to when I can’t see the floor beneath me, but hey – she was sobbing and he looked happy, so props for pulling it off! On your elevator ride up to the top of the SkyDeck, you’ll see a video that notes when you’re passing other massive global monuments, from giraffes or dinosaurs to the Eiffel Tower. It’s definitely a worthwhile perspective on the city!

What to do in Chicago: A Weekend City Guide

What to do in Chicago: A Weekend City Guide

What to do in Chicago: A Weekend City Guide

Day 4:

Coffee at Two Zero Three. This is Virgin’s resident coffeeshop + wine bar, so it’s basically heaven. If you’re passing by the Loop, it’s definitely worth a stroll down the street – it’s got the best atmosphere for working and/or catching up with friend! We ordered room service coffee (and room service lavender matcha lattes…bless) every single day in the city and stopped by for salted caramel lattes in the afternoons – seriously the best SCL’s either one of us had ever had! We got those + homemade blueberry muffins for our trip back to the airport – all about that travel grub. ๐Ÿ˜‰

Mural sightseeing. I had no clue Chicago had SO many beautiful wall art on the street. We found a few while there, but it’s a fun adventure to just drive around the city spotting the bright painted walls. More from those shoots to come, but again, shoutout to my Snapchat fam who saw the Dumpster shenanigans. ๐Ÿ˜‰ (Follow me here @ erica_lig if you aren’t already!)

 

Have you ever been to Chicago? What are your favorite things to do in the Windy City?

I’d lovelovelove to hear your own personal faves in the comments section! And do you like little weekend snapshot city guides on CUR? I’ve been getting the chance to travel more for work, so if this is helpful for y’all, I’d be more than happy to whip up guides for your own excursions. Just let a sistah know, mkay? ๐Ÿ˜‰

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