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A Houstonian’s Guide to: A Weekend in Chicago

Chicago is a huge and diverse city — every time I visit, I have a different experience. I’ve celebrated Christmas at the Christkindlmarket, played in the snow, watched the river get dyed green and bottomless brunched in the spring. Safe to say, I’m a huge fan and take every opportunity to grab a cheap flight from Southwest Airlines — I’ve flown roundtrip for as cheap as $150.

Here are some tips and ideas for your next Chi-Town trip.

Know before you go

  • Pick your neighborhoods. There are over 50 neighborhoods that all have different personalities and reputation. There’s River North (a part of downtown) that’s great for going out and has a lot of touristy-worthy spots. Other fun places to visit: Wicker Park, Lincoln Park (you’ve probably heard of this one), Boystown (a gayborhood), Bucktown, Logan Square and more. It’s pretty easy to bounce around, but you can definitely pick a few to spend most of your time in.
  • The El is definitely do-able. I’ll preface this with the disclaimer that I’ve only taken the El a couple times. It’s pretty cheap and easy to navigate — literally just type where you want to go in google maps but ignore busses if that’s not your thing. I mainly got around using Uber or Lyft — there’s Uber Pool and Lyft Line that makes it cheap and warm.
  • Check the weather! When I went in December, it was 17 degrees and snowing when I landed. In March, it was 30s and had just snowed too. Pack accordingly! Waterproof boots, heavy jacket and lots of layers.

Touristy to-dos

SkyDeck: It’s $22 to go up to the 106th floor in Willis Tower. The line when we went wasn’t so bad, but be prepared to wait — especially on a clear and pretty day (which ours was not).  I’ve done both the Top of the Rock and the Empire State Building in NYC, so I wasn’t really thinking it was scary or anything — until we got close to the SkyDecks, which hang over the city by a couple feet. Still, I can’t say that I was too freaked out. Honestly, it all moves so fast (mainly because people are waiting), so I didn’t have time to be freaked out. I think this is a must if it’s your first time to the city!

The Bean and Millennium Park: Both are also must-see attractions, but these are free! The park is so festive in December — huge tree, snow everywhere and ice skating! A snow-covered bean isn’t that cute, but hey! at least the crowds were managable. We walked around until casually someone sang to us, “do you wanna build a snowman?” Like Elsa, we declined, but we did watch the magic happen.

ChicagoThe Chicago Theatre: You don’t have to go to a show to take a cool shot with the infamous Chicago Theatre sign.

Second City: I couldn’t go to the comedy capital of the world and not see comedy, right? I really didn’t know what I was in for, but it ended up being a sketch show that had some improv opportunities. Most of the improv was pretty hilarious, and I loved a lot of the sketches. There was a lot of election/political sketches that reminded me so much of SNL. The show was 2 hours long and had an intermission. I laughed my butt off during so many different sketches, but I will forever chuckle over one in particular: The Bassman.

Magnificent Mile: Downtown shopping akin to 5th Avenue in New York!

Where to eat and drink


From deep dish and bottomless brunch to Chicago-style hot dogs and breweries, your complete guide to eating your way through Chicago is here:

Where to Eat and Drink in Chicago



Lollapalooza Chicago

One of the US’s biggest summer music fest is in the heart of Downtown Chicago! It was on my bucket list to go and I jumped on the opportunity. I put some temporary purple dye in my hair, bit the bullet and bought a 4-day, $400 ticket and headed north!

Know before you go

  • It’s dirty. It hadn’t rained in Chicago in a minute, so the dirt clouds are REALLLL. And they only got worse as the thousands of people trampled through every day. Don’t wear your nicest things.
  • It’s hot. Don’t be fooled by the fact that Chicago is 1100 miles north of Houston — it’s sweaty and sticky in the summer too. Some years there’s better weather, but for me, it may as well was Houston hot. The trendy thing to do is wear as little clothes as possible.
  • It’s expensive to drink. I mean, obviously. We crunched the numbers and the wine was the best deal for all day drinking: $30 cupcake wine (one white, one red, rose and prosecco) was the best deal for volume, price and ABV. It’s one full bottle that comes in a carafe/sippy cup that’ll last you a few hours for sure! It was $8 for a low cal seltzer drink, and around that for beers too.
  • It can be expensive to eat: It’s all about finding the most efficient options and there are SO many foods to choose from! A $4 deep dish slice was probably the best deal, but feel free to experiment yourself!
  • Bathrooms vary in grossness. Yes, there are the normal gross portapotties that are hot and disgusting, but there are also really nice flushable ones that are worth walking to! I gotta say, never once did I not have toilet paper or hand sanitizer to use, too! Great job, Chicago!
  • The lay of the land. There are 7+ stages at Lolla. Two big ones (Grant and Budlight) at either end of the LARGE park, each with a mid-sized stage (Lake Shore and Tito’s) right there too. Then, there are three small stages scattered around, plus more intimate stages by other sponsors. The stages all have their own personalities, especially Perry’s, which is just EDM and House music all day every day with the teens raving in there. I avoided at all cost. Then, there are bars and bathrooms EVERYwhere, but the bulk of the food is on one side of the park — there are so many options!
  • Use the app! I loved the app so so so much. you can pick your artists you wanna see and add them to your schedule plus utiliza a ton of other things to do!


  • Go cashless. I almost forgot this tip bc it’s so obvious to me that everyone would do this! You can hook a credit card up to your wristband and paying for things is just one easy tap. You also get carded when you buy your first drink, and then they give you a blue wristband to indicate 21+. Ideally that means you can go the whole time without your cards, but I brought mine just in case. Which was good, because some lady did card me later bc she thought I looked young. OK, ma’am, I look NOTHING like all the teens at Lolla.
  • Take. The. Train. Wish I would have better done this, but my friend’s place is almost an hour away from the fest via train, so we ubered every day.
  • Eat and drink before you go! We started every day with a big meal! It was nice not to have to eat until later in the day.
  • Go bagless!!!The game changer was not bringing a bag… yeah, it sucked having heavy pockets, but you don’t need a wallet — your wristband is hooked up to your credit card — just a spare card and ID you can tuck into your phone case. We did also carry portable chargers, and I highly recommend that. Other than that, I had an It’s Not Houzie and was all set! Note: Fanny packs are bags, even though they totally let people in with fanny packs before. Grr…
  • Need a bag? Lolla shop sells $3 totes! A souvenir and a lifesaver if you are tired of carrying things in your pockets.
  • And/or early. If you’re showing up before 2 pm, you can take a bag and probably be fine. Once it gets closer to 4/5, it’s a madhouse trying to get in.
  • Secret Monroe Street entrance is CLUTCH. It’s definitely a smaller entrance from the main Michigan Ave entrance. We waited SO LONG the two days we got in at the main entrance — even bagless! Monroe entrance seemed to be more unknown and I literally walked right through!
  • Don’t lose your phone, but if you do, lost and found is pretty legit.

Worth it? Yep.

I was honestly super impressed with how Chicago ran this thing! 100K people per day storming downtown sounds like a huge undertaking logistically, but the city is well equipped! Sure, getting an Uber at the end of the show is quite an undertaking, but we managed to do it just fine all four days!

It was such an incredible (and incredibly daunting) four days. I’m SUPER tired after the trip, but I loved, loved, loved all the (25+) bands I got to see and all the cutie pictures I got to take. I’ll be wearing my Lolla shirt to sleep and reminiscing on the weekend for potentially ever.

St. Patrick’s Day in Chicago

Chicago has one of the biggest populations of Irish people outside of Ireland! No joke! It’s a fun time.

Watch the river get dyed green

The river will be green the whole weekend, so you’ll have plenty of time for pix, but I LOVED getting there early and watching the dying process. Head to the Columbus Bridge (Columbus and North Water) at around 8:30 am. The dye goes in at 9!

Go to the parade

The parade is in Grant Park (which isn’t very close to the river like you’d think). It starts at noon. We actually skipped this part of the day for bottomless mimosas and had no regrets.

Do a pub crawl

One of the biggest ways to celebrate the holiday is an all-day pub crawl. There were SEVERAL to choose from. If you do want to go out in Chicago on St. Paddy’s Day, plan on one of these. A crawl wristband gets you into bars quicker and some of the lines were LONG. Also note: These crawls start at like noon. It’s definitely a day drinking thing.

Christmas in Chicago

You’ll freeze but fall in love with everything you do!

Ice skate in Millennium Park

There’s a small rink in front of the bean, but if you go into the park there’s a longer ribbon rink.

Take a picture with the big tree

Also in Millennium Park! Hello Christmas Card!

Shopping at the Christkindlmarket

This market is free and right by Millennium Park. It’s usually very busy, and only get busier the closer you go to Christmas, but I still think it was worth it! For us, it was less crowded (thanks snow!). Your shopping list must include: Mulled wine, candied nuts, large cookies with weird things written on them, cheese, apple cider and all the hand-crafted goods! You could also eat a full meal here! We didn’t. Thanks snow.

Other things to try

Treat yo’self at Blueberry Moon

I figured since Chicago would be cold and dreary, a treat yo-self day was in order. I visited Blueberry Moon in Lincoln Park, which I would come to find out, basically your one-stop shop for all beauty and spa things. Need highlights? Get ’em. A mani-pedi? Done. Facial or body wrap? Sure, why not?

I honestly think Blueberry Moon was my favorite part of my visit. I got a Dual Exfoliation Peel facial (a specialty) and a mani-pedi. We started with the facial, and my esthetician was a sweetheart. The facial reminded me of Milk + Honey, actually! Except everything at Blueberry Moon is Aveda products… and you can buy them in the store or online if you fall in love.

I was a little scared, since the treatment had “peel” in the name. My head went straight to “chemical peel”, but it needn’t have. Zero parts of the facial hurt or stung — everything was so gentle! And my face was not a bit red at all!

Next was a pedi (followed by a mani so that my toes would have ample time to dry before going back into the boots!). You can’t be too creative with a mani-pedi, but I loved the little nail nook and all the Aveda products used! My non-shellac nails lasted two weeks (what a Christmas Miracle!).

I’d be remiss to not mention one of my favorite things at Blueberry Moon: Their amazing Aveda tea. I got a glass as soon as I walked in, and it was warm, sweet and delicious. I wanted to take some home with me!

Cheap and quick alternative: Mud. Facial Bar specializes in mud facials. You sign up for a 30-minute appointment for about $50 a facial. Total pampering follows.

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13 thoughts on “A Houstonian’s Guide to: A Weekend in Chicago

  1. Really awesome and informative post! Signing up for a few gym classes is actually a really great idea. I’m also really impressed with the Christmas Market. I’ve been visiting a handful of them in Sweden and Germany this year, and Chicago really captured that European Christmas Market atmosphere.

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  5. Great read, I’m visiting for the first time this summer so I’ll add some of these suggestions to my list 🙂

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