3 BEST travel tips for Chicago

If you follow me on Instagram, than you likely followed along on our trip to Chicago a week ago. And y’all… it was one of the most fun trips we’ve been on!

We decided to mix things up a bit and take the train (Amtrak) to the Windy City. And let me tell ya, taking the train is an experience in itself. We boarded the train in Richmond on Saturday morning and rode up to Washington DC, where we hopped on another train that would take us the 16-ish hours to Chicago. We decided to go with a little roomette, which made for more cushy traveling – more privacy, actual beds, private bathrooms for just our sleeping car, meals included, and a car attendant that helps you with literally anything you need… all the things that make 16 hours on a train a little more bearable. And honestly, we thought it was super fun. I will say this: spending a night on the train is not for the easily motion sick, you are constantly rocking back and forth and when nighttime falls, there’s really no horizon to be seen out the window. Ugh.

Before our trip, we did a little research about Chicago so we arrived with a general list of things to do. But mostly we just figured it out as we went. Today I’m sharing my 3 best travel tips that helped us navigate the Windy City and make the most of our trip!

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Get an unlimited CTA pass

We decided to forgo the cost of renting a car (plus the headache of parking in a major city) by taking public transportation. If traveling with the masses isn’t your thing… scroll on to the next tip. But if you don’t mind a little people watching and relying on good ‘ole public transportation then keep reading!

We were SUPER impressed with the metro/El/buses in Chicago. It was clean, quick, and I never once felt unsafe. As soon as we arrived at the Amtrak station, we headed to the nearest metro station, where we learned that we could purchase an unlimited 7-day CTA (Chicago Transit Authority) pass. Major score! For $33 (each, because each person must have their own card), we hopped on and off the metro and city buses any time and as many times as we wanted. There was absolutely zero worrying about if we had enough fare on our cards. It took so much guesswork out of our trip. Also, I’m honestly not sure how much individual fare was but let’s say each time you hopped on the metro it cost $2. In just 16 rides that would have paid for itself. And I promise you we rode WAY more than 16 times.


Get a Citypass

Just trust me on this and thank me later. The Citypass was single-handedly the BEST investment we made this trip. And it turns out there are more cities that have the Citypass than I realized. But basically you can purchase a Citypass which gets you discounted entry into five must-do museums/attractions in Chicago. For $106 each, we got into:

The Field Museum (VIP entry with free entry into the paid special exhibits and a 3D movie)

The Adler Planetarium (two free shows)

The Museum of Science and Industry (free entry into the Coal Mine exhibit and a flight simulator)

The Shedd Aquarium (free 3D movie)

The Skydeck at Willis Tower (VIP entry – skip the line to the top!)

If we’d purchased admission alone, we would have spent at least double that because each museum is between $20-$40 per person. We felt like it was an incredible deal for what was included. I should also add that two of your options were choices between two museums. Instead of the Planetarium and the Museum of Science and Industry, we could have chosen the 360 Chicago Observation Deck and the Art Institute of Chicago. And if you wanted to do ALL of the options and not choose between two, you could get discounted admission rates into the other two. Also, we got a discount at some of the gift shops with the Citypass. Hands downs worth every penny.

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Eat local

So I saved the best for last. Throughout our trip, we joked that we were there for the food. Because it really was a culinary adventure. I mean… we ATE. And we ate some really great food. I’ve mentioned it on my blog before, but we have a pretty strict policy of only eating at local restaurants when we vacation. We try really hard not to stop into corporate chains, not because we don’t like their food. It’s just… well we’re only in Chicago for a short time, I’d rather eat something that I can’t get back home, ya know? So the easiest way to sum up this section is with a list of the places we ate.

Lou Malnati’s Pizzeria (deep dish pizza)

Giordano’s (deep dish pizza take two)

Limitless Coffee

Stan’s Donuts

Ramen-San (this might have been one of my favorite places we ate. I could have eaten here again and again!)

Duck, Duck, Goat (a trendy take on chinese food)

Portillo’s (Chicago dogs, basically local fast food but oh so good. We ate here twice.)

Burger Bar

Ballast Point Brewery

Cone Gourmet Ice Cream

Fairgrounds Coffee and Tea

La Fournette (cute little french cafe, great macarons)

Uncle Joe’s Jerk Chicken (probably my second favorite restaurant, amazing jerk chicken, total hole in the wall)

Xurro (churros on the Navy Pier)

Public House

There ya have it, my top three tips for planning your next trip to Chicago: get an unlimited CTA pass, buy a Citypass, and absolutely eat local! We thoroughly enjoyed Chicago and would totally go back in a heartbeat. There’s still so much to explore and we could easily spend another full week there. Plus the amount of restaurants still on my to-try list is endless.

And in case those tips weren’t enough, I’ve got a few bonus tips for ya that won’t make or break your trip but might be useful:

Stay local

We like to Airbnb it any chance we get on our vacations. And here’s why: generally we’re searching for a home that has a kitchen, which helps us save a bit on food. We’ll plan breakfasts in so that we can spend a bit more and have lunch/dinner out. So having a fridge to store some milk and necessities is key. We also like having the option of cooking a low-key dinner if we wanted to head back early. Generally, we’ll plan our meals a little better and not eat out as much as we did in Chicago… but we knew we would be in for a culinary adventure. 

We stayed in northern Chicago, about a 40 minute metro ride in each morning, but it honestly didn’t bother us that we were a little farther away. It was a place to rest our heads after miles of walking each day and it was super close to the lakefront. Also, we had the sweetest host. And I like to think about it this way: I’m helping support a local business by staying local.

Take an architectural boat tour

This was recommended to us by a few people… and it didn’t disappoint. We found a Groupon at the beginning of our trip. It was a 90 minute tour up the Chicago river and back, narrated by a guide that was very knowledgeable in the history and architecture of the city. It was a great learning experience and gave me a whole new appreciation for the city.

downtown chicago - nicole guido

Chicago Hashtag List

Here’s the Chicago hashtag list I compiled for my Chicago Instagram posts!

#chicagolove #chicagofamilyphotographer #chicago
#chicagoaquarium #chicagoengagementphotographer #summertimechi
#chicagotourist #chicagoengagement #chicagoland
#milleniumpark #chicagofamily #chitown
#chicagobride #windycity #eyeinthechi
#thebeanchicago #thebean

Most of you know that Ben and I REALLY love to travel. Check out our recent adventures below:


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