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.
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.
The 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!
This was a busy spot when we went. I feel like Half Acre is the Karbach of Chicago: The beer is great and it has a great place to hang. I got two flights (because I thought I was sharing). Unfortunately, there weren’t any labels, but I liked all the different beers! I definitely recommend going on a Saturday morning to do the tour!
Deep dish is a MUST! But fair warning: It’s a whole experience. The pizzas take 45 mins to make, so order up and tuck in. There’s a whole debate in Chicago between Giordano’s and Lou Malnati’s. Both are good for different reasons and both have locations across the city. Tho, if I had to pick…. Giordano’s is my fave.
Though I loved Giordano’s, Lou was my first bite of deep dish and I’ll always love it for that. We got the classic (and added green peppers). It was cheesy and delicious. A total knife-and-fork dish — hands would be impossible. I ate two pieces, with no shame. But I will say, those two pieces were super filling. One pizza and one bottle of wine later, I was obsessed and ready to be rolled right out of the restaurant.
There was a long wait at Giordano’s in downtown Chicago during St. Paddy’s Day, but we got to order our pizza while we waited for our table, so we were eating within five minutes of sitting down. The crust is really what sets it apart for me — I ate twoish pieces and wanted so badly to be able to cram more in because so delish!
Brunches and bites
The Hampton Social
You’ve seen this one on Instagram. It’s got the “rosé all day” sign and the cutest nautical decor. I went for brunch, but it’s definitely cute for dinner or lunch too. I got the fish tacos (not exactly a Chicago specialty) and they were surprisingly good. You gotta go for the rosé, but I also loved the frosé.
For just $27, you can get 2 hours of bottomless mimosas and an entree at this lovely downtown eatery. 10/10 would recommend. That’s probably one of the best bottomless deals. It’s French food, and pretty delicious at that.
Zella is a little more expensive but it’s all you can drink AND eat. For $50, you can literally spend hours at Zella. And we did. We got there around noon and closed the brunch down at 3. Zella, which has a beer garden patio that was closed and covered in snow when I visited, usually has a line out the door. But we sat inside (obviously) and near the TVs (the Texans were on).
The food was ehh, aside from the mac and cheese. That was some of the best mac I’ve ever had. The mimosas were also just solid (although my table must have split a dozen carafes, so we didn’t hate it), but Zella’s saving grace was its throwback playlist. So many great tunes — the kind you forget you know all the words to. Everyone in the bar was so, so drunk and so, so happy.
Portillo’s is another rite of passage in Chicago. You gotta get the beef sandwich and/or the chicago-style hot dog. This is a specialty: yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt all on a poppy seed bun.
Dinner at Purple Pig
We got super lost finding The Purple Pig, and when we did find it, there was a line out the door, which wasn’t great for us, since we were in a rush to get to Second City. Thankfully, there were exactly two free barstools, so we grabbed them. A quick Yelp search informed us that the pork shoulder was one of the best things on this earth, so we ordered that, a half bottle of wine and some spanakopitas!
All the stress and craziness finding the place was so so so worth it. The pork literally fell apart on the plate, and the mashed potatoes were amazing. Honestly, one of the best meals of my life.
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.
Out on the town
During the winter months, Chicago peeps don’t go out too much and definitely don’t do the whole bar crawl thing. Brr. Apparently though in the summer or late spring, everywhere is popping. There are a few bar-centric hoods of Chi-Town. Here were our options:
- Division and State: Lots of divey fun bars.
- Old Town: Midwest bar central, meaning all the sports bars.
- River North: More upscale — people dress up!