Chicago Traveler Blog

Chicago Traveler Blog

Things to do in Chicago When It's Raining

6/18/14 | by

Everyone hopes for the best weather possible when you're on vacation, but when you plan your trip months (or weeks) in advance, you never know just how the weather is going to turn out! The lucky ones get to Chicago when the sun is shining the summer or the snow is falling beautifully in the winter, but what about all of us who finally get off the plane for our fabulous vacation and it's pouring outside? WHAT THEN?!

Well, if you're in Chicago, you just buy an umbrella (or poncho if you're really trying to be touristy) and go to town as you were. Sure, it might put a little damper on your boat tour or stroll through the park, but there is still plenty to be done, and some of the Chicago tours even still go on! Here are all the best things to do in Chicago when it's raining - so take note for your next trip, just in case. Most of them are things that some of us like to do even on the best of days!

Make a List, Check it Twice

Then head to Magnificent Mile for a day of shopping in Chicago. It's easy to spend every second of your trip on this popular Chicago past time, even without spending all of your money. While it may be tempting to take home every pair of designer shoes and tacky shotglass you walk by, spending hours in these stores doesn't have to result in the foreclosure of your home just because there isn't anything better to do on a rainy day. For all your different needs, head to the following places:

  • Michigan Avenue: Where the rich come to indulge and the poor come to... pretend they are rich. High-end designer shops, those famous department stores we all know and love (or would love if we could afford to be known there) and a few familiar chains to fill in the holes.
  • Lakeview: Full of thrift stores and inexpensive boutiques (because where else can you find those but Chicago.)
  • Lincoln Park: Native Chicago shops with local merchandise and things you won't find everywhere else. The stores vary, but every shopper on any budget can find something to take home with them here. 
  • Bucktown: For all the trendy hipsters that don't need the real brand label - just close enough to send the message from afar. It's a classic case of Toms vs. Bobs. 

Get Lost in a Chicago Museum

Has it been a while since you saw Sue? She's probably missing you! What better way to spend a day in Chicago than walking around the exhibits at one of Chicago's biggest attractions - the museums! From the Field Museum of Natural History to the Children's Museum, there's something for everyone to waste a rainy day away in!

  • Here's a list of all of the Chicago Museums, because it would be impossible for us to recommend just one.
  • There are several Chicago passes to the city that provide discounted admission to several museums and other Chicago attractions that you can use throughout your trip if you really want to get the full Chicago experience.
  • Don't neglect the Shedd Aquarium! Rain or shine, these fish don't know the difference - but they are worth the time to see regardless.

Food Tours

If it's drizzling outside, even the biking food tours go on! Yes, Chicagoans (and Chicago Travelers) are serious about their food, and a little rain is not going to stop us from filling our belly! Whatever it takes to get to the next slice of pizza and lick that last bit of frosting off our fingertips, we will do it! Don't hesitate to take one of the Chicago Food Tours when it's raining outside! If anything, it makes them even more interesting!

  • Good Times Historic Bar Tour: Rain or shine, you will get your booze, just make sure to keep the raindrops out of your glass - you don't want anything watering down these brews! While this is a walking tour, when it's raining outside, they adjust accordingly and the only thing drowning by the end will be your liver. Not really, they keep it civil here. What do you take us for, some kind of frat boys?
  • Bikes, Bites and Brews: Rain or shine, you can ride your bike from your pizza to your beer and as miserable as that may sound to some people, you won't be complaining about it, we promise! Bobby and his crew make all their bike tours fun, and Chicago's food scene doesn't have to work hard to take care of the rest of it.

Stay in Bed All Day Long

Or at least enjoy all the amenities of your hotel! Many have indoor pools, spas and don't forget the comfortable beds and HD TVs that will provide hours of entertainment that your normal life doesn't allow. 

Enjoy the Chicago Nightlife

Chicago has some great nightlife, and hopefully a little waterworks (at least this kind) isn't enough to keep you from enjoying it.

  • Head to one of the shows on Broadway in Chicago or see someone that's just passing through. So many comedians, bands and performers are always stopping in for a night or two while you're here. Sure, you might have seen Chris D'elia doing stand up around the corner from your home, but have you seen him being wildly mediocre yet still charmingly handsome in Chicago? Probably not... but you totally can. Check out a Chicago Theatre to see who will be in town while you're here.
  • Chicago has lots of great craft beer bars to enjoy a good brew and some local dives to get some great deals on binging all night. Why remember every moment of your trip when you can find dollar beers and black out? (We totally don't support these actions, but they are not uncommon in some bars.)
  • Chicago is famous for their BYOB restaurants! Find a great one near you and get the nightlife started at your table!

As you can imagine, this only breaks the ice for all the great things to do in Chicago on rainy days. Don't let a little moisture in the air spoil your trip - and for all you photographers, be sure to step out and see the beautiful city before, during and after every storm! You're sure to go home with something that will earn you 50 likes on Facebook and a jealous ex-girlfriend or two. Let us know what your favorite things to do when it's raining on your day in Chicago by joining us on Facebook, following us on Twitter or even keeping up with us on Google+!