A question EVERY traveler will ask each other is, “Where are you from?”.
It’s a simple question but when you’re 8, 9 plus months into your travels with no exact plan of when or if you will return “home”, you start feeling like you have to add to your response. A simple question becomes so complex; you start questioning what is “home”?, where is it?, is it the last place you permanently lived at? where you were born? or do you go the cheeky route and say something like, “Well today, this is home.”
I decide that these strangers asking me this simple question required a disclaimer, “Well I’m from Chicago but haven’t lived there since I started traveling x months ago”. Sure, it gets the job done but internally the answer never sat quite well with me for the reasons mentioned above. And did I mention I’m Guatemalan too?
On the 15th month of my Girl Takes Mundo journey, I finally returned “home” and while I’m here to shout it from the rooftops that being a traveling nomad is G R E A T…having a place you call “home” and actually returning to it makes appreciating not only your travels but your “home” city even more.
While traveling, I discovered very quickly that having a local guide helped me really explore a country/city to its fullest and so, no travel blogger could fully call themselves a travel expert if they can’t do this in their own city.
Consider This My Ultimate Guide For Visiting Chicago!!!
Comment in this post if you have questions on making Chicago your next holiday or on any of the other countries I’ve called “home”. See my calendar here.
- The best time to visit Chicago is during the time locals call, “Summer Time Chi”. “Summer Time Chi” happens during June – Mid September when we have the best weather. If you travel to Chicago during this time, you can guarantee you will get the best taste of what the city has to offer and you will really see how locals leverage every moment of their 100 days of summer. Join in and do as the locals do by filling your days with tons of activities.
Moving around in Chicago is shockingly very easy. Public transportation is a common way of getting around as a tourist in this big city but also economical too.
Chicago’s train system is very well organized and able to get you to all tourist and local spots. When you arrive, ensure you pick up a Ventra Card (Available for purchase at all train stop kiosks and refillable for all your train and bus travels in the city.) The card will cost you .50 cents USD and each ride is $2.50 USD. Just ensure you check the schedule for operating times as only the “Blue Line” runs 24 hours and many others stop operating at 1:00 am then resume operation anywhere between 4:00 am – 5:00 am depending on line.
Learn more about using public transportation in Chicago by visiting the Chicago Transit Authority website here.
If the train can’t get you to your location, buses can certainly get you there. (Tip: Cost for each ride is $2.50 USD and you can use your Ventra card to pay for your bus rides too.)
Learn more about using public transportation in Chicago by visiting the Chicago Transit Authority website here.
Uber is available in Chicago including the carpool option, which is perfect for solo travelers or those traveling with a party of 2. If you have a bigger party this may also be cheaper than using public transportation. I always price out even as a local.
Tip: Never used the car share app before? Use my code, “r83uv” when setting up your Uber account to get a discount on your first ride.
If waiting for an Uber isn’t your style, hailing a taxi is still done here. If the trip is a short ride ensure they will let you pay with card if this is how you intend to pay. Legally they should accept all rides and all forms of payment but cab drivers can get quite particular around short rides and payment options so be sure to ask first.
Have more in your party and want to venture outside of Chicago? Consider renting a car. Drivers in Chicago for the most part are easy to share the roads compared to drivers in other cities in the US. The only downside is that city traffic has increased quite a bit in the past years.
Wondering where else you could visit near Chicago?
- Detroit has become a big name in the art and music scene making this a great road trip.
- If you are looking for nature; Wisconsin is calling your name. Wisconsin Dells in particular is a fantastic weekend getaway for families with water-park, theme parks and places for camping.
Tip: If you like beer, don’t miss trying “New Glarus” beer as it can only be found in Wisconsin. Be sure to pair it with cheese as this is what Wisconsin is known for.
- Starved Rock National Park is the perfect place for hikes outside of the city. Make a day out of it and check out some of the wine shops around the state park and for those under 21 there is a cute candy and cupcake store in the town closest to the park to curve that sweet tooth.
- Swallow Cliff Stairs – Keen for a workout with spectacular scenery? Then Swallow Cliff Stairs in Palos Park is just for you. These stairs are a no joke workout even for tourist personal trainers.
- Hitting up another country from Chicago is also very doable as Canada is our neighbor and cities like Toronto and Niagara Falls are just a short drive away. (See what I got myself into in Canada here.)
Chicago is one of the major international airport hubs of the world which means many airlines make stops here, making it easy to get here from any corner of the world.
English is the predominant language in Chicago but don’t be surprised if you find yourself exploring neighborhoods more predominantly Latino like Little Village, Pilsen and Humboldt Park where Spanish may be the first thing you hear or what you will hear a lot more while there. But need not worry trying to use your best Espanol as there will always be someone who speaks English.
Additionally, did you know that the place with the second biggest Polish population after Poland is Chicago? That being said, if you find yourself in certain neighborhoods such as near Midway Airport, Portage Park or Belmont Craigin you can guarantee you’ll hear Polish as well.
Places To Stay
- Chicago Athletic Association – A great hotel if you are looking to be morphed into time as this hotel has a very 1920’s feel.
- Radisson Blu Aqua Hotel Chicago – This beautiful modern hotel has all the amenities one could ask for including a gym, indoor/outdoor pool, bar, sauna and steam room. I had a stay-cation here and was left wanting to extent my holiday.
If you are coming with a group or wanting to have a feel of home than an Airbnb is a great option to consider while in Chicago. Search neighborhoods like “Chicago Loop”, “Pilsen”, “Wicker Park”, “Lincoln Park” and “Logan Square” as these are great areas to stay while visiting Chicago.
Tip: Have you tried Airbnb? Sign up with my link HERE to receive up to $55 USD off your first trip.
Where To Visit
Navy Pier – Old port turned tourist attraction that has shops, restaurants and great views of the city. During the summer they have fireworks every Wednesday and Saturday evenings and if little ones are with you, don’t miss out on checking out the Children’s Museum while you are there.
Magnificent Mile – Chicago’s premier commercial district full of upscale shops, restaurants and hotels.
The Bean – Originally named “Cloud Gate” by its artist, this sculpture has become a must visit when in Chicago.
Millennium Park – One of my favorite places to bring friends who are visiting is this beautiful park in the center of the city where “The Bean”, Buckingham Fountain”, and “Maggie Daley Park” are located.
Tip: If its summer don’t miss checking out the park’s calendar of events as there is always something happening including free movie nights, concerts and workouts.
Buckingham Fountain – An iconic Chicago landmark in the center of Grant Park and considered one of the largest fountains in the world.
Maggie Daley Park – A great park for kids and kids at heart with tons of kid friendly sections including a pirate ship, mini golf and wall climbing.
Tip: If it is winter when you visit, go ice skating in the skate ribbon or in the skating rink in front of “The Bean”
Sears Tower – Once the tallest building in the world, the Sears Tower also known as the Willis Tower by tourists is a great observation deck with views of the city and beyond.
John Hancock – Great observation deck with views of the city and lake Michigan.
Art Institute of Chicago – I love art and this by far has to be my favorite museums in Chicago and probably the world. It’s beautiful inside and out and holds some of the best and most recognizable art collections in the world including, “A Sunday Afternoon on the Island of La Grande Jatte” by artists Georges Seurat.
Mexican Museum of Fine Arts – A great museum to immerse yourself in Mexican art and culture but get a better understanding of the Latino community in Chicago. Big perk is that this museum if free all day, every day.
Tip: If visiting around October, their yearly Day of the Dead exhibit never disappoints.
Science and Industry Museum – Another one of my favorites when it comes to museums as it has many interactive activities and is the largest museum in the western hemisphere making this a great way to spend the day.
Garfield Park Conservatory – One of the most largest botanical gardens in the US and often called a “Landscape art under glass”. It surely doesn’t disappoint and a big plus is that its free to enter too.
Tip: If planning your visit and coming with kids, most Wednesday’s they have activities specifically for kids. Refer to the website to confirm if operating as they tend to change the calendar during special events or holidays.
- Bicycle ride on the south side part of the lake.
- Check out a baseball game.
- The Sox stadium is perfect if you want to take in some tailgate action outside of the stadium before the game.
- Go to the iconic Wriggly Field to get a taste of old school baseball seeing the legendary Cubs play. Don’t forget to get into the action with a pregame in the many bars around the stadium.
- Stroll through the Pilsen neighborhood during the day for some fabulous street art by Chicago favorites.
- Take in some comedy at the famous Second City where legends like Tina Fey, Chris Farley, Mike Meyers and Amy Poehler have studied.
- Stroll through the Chicago River Walk and if you get lucky, catch the bridges separate to let ships through the river.
- Visiting in late November/December? Check out “Zoo Lights” in Lincoln Park Zoo for a lovely light display to ring in the holiday season.
- Visit the Bahía Temple outside of the city and don’t forget to pack a picnic to enjoy along the lake. (If you have time be sure to visit the “Home Alone” movie house which isn’t far away.)
- If visiting in the summer, be sure to take in the rays at “North Avenue Beach”. This is a lively place to catch some sun and enjoy the lake despite it being called “Beach”.
Where & What To Eat
Pequods – Tourists tend to check out Giordanos, Pizzaria Uno and Pizzaria Due. But people who want to try one of the best deep dish pizza Chicago has to offer, go to Pequods. Yes, you may have to wait a bit to be seated if you go during peak hours and yes, you will then have to wait an additional 40 minutes for your pizza to cook but once you try a slice you will know why it was worth the wait.
Tip: They offer a great lunch time special during the week between 11 am – 3 pm. For $4.95 you get a 7′ pan pizza and non-alcoholic drink.
Home Run Inn – If you are looking for authentic non deep dish Chicago style pizza then this is the spot for you. Delicious buttery crust pizza and their frozen pizza’s sold in markets are also a top favorite by locals for at home pizza options. If you are staying in a place with a kitchen I highly recommend picking up a frozen pizza and seeing what all the hype is about.
Chicago Pizza and Oven Grinder Company – For another take on deep dish pizza, the Chicago Pizza and Oven Grinder Company will not disappoint with their famous and equally delicious pizza-pot-pies. FYI: This is a cash only place and since this is a small venue there will most certainly be a wait so do yourself a favor and arrive when they open or during non-peak hours when the wait won’t be as long.
Small Cheval – The sister restaurant of “Au Cheval”, aka considered to serve the best burger in the US offers a scale back menu to their infamous older sister restaurant. The same delicious and yes, best burger in the US, fries, shakes (Don’t forget to add a shot and make it boozy) and drinks minus the 4 hour wait at “Au Cheval” which unknowing tourist will do. SERIOUSLY, pre-vegetarian me was a burger connoisseur and can vouch for this burger. It REALLY is the best burger and I’ve ate burgers all over the world.
Portillo’s – This restaurant chain is known for serving Chicago style food such as the legendary Chicago style hot dog (hold the ketchup), Polish sausages and Italian beef.
Must Order: Italian beef dipped with peppers and either a slice of their legendary chocolate cake or their chocolate cake shake.
Weiner Circle – The infamous place to grab a Chicago style hot dog (hold the ketchup) after a night out. This tiny place serves up the dogs with a side of sass from the staff. While locals can testify to having come here before, this spot really is a place for tourists. Still a must to check out if you have the time.
Ethnic Specific Cuisine
Mr. Greek Gyro – The best place to have a Greek Gyro is from this no frills spot in Greek town. For those who don’t know what a Gyro is, please Google it and don’t you dare say it looks like a doner kebab without ever actually trying one. I and every Greek person including Mr. Greek himself will haunt you down. Despite what the website says this places closes at 3:30 AM every day which means you can always head here after a night out. (Admittedly, this is the only place in the world that the veggie eater in me takes a pause from her vegetarian ways to eat meat and even after eating a Gyro will have no regrets. Yes, It’s that good!)
Jibarito’s y Mas – Many may not know this but my favorite cuisine is Puerto Rican food and sadly for me, outside of the the United States and Puerto Rico there are only a handful of restaurants around the world that offer some sort of “Puerto Rican” cuisine. (FYI: During all of my Girl Takes Mundo travels I only found a stall in Slovenia’s Friday Food Market that sold a Jibarito; a fried green plantain sandwich filled with meat, cheese, lettuce and tomato.) Jibarito’s y Mas is single handily my favorite Puerto Rican restaurant and it is for many Puerto Ricans here in Chicago so you know the ultimate seal of approval is there. If you come to visit me in Chicago just know we will probably end up here because its rare for people to eat Puerto Rican food for the reasons stated above and because I’m always trying to get my fill while I am here.
Must Order: Jibarito de lechon (roasted suckling pig) with arroz con gandules (rice with pigeon peas)
Mariscos El Veneno – I’m a sucker for crab legs and this BYOB seafood place is my favorite in Chicago. Buttery, spicy and with Mexican size portions its recommended you bring a friend and share these delicious crab legs.
La Vaca – Delicious taco and margarita spot in Pilsen. Best night to go is on Tuesday for their $2.50 USD taco special.
Must Order: Lomito, La Vaca, Big Boss, El Green tacos and wash them down with a mango margarita. Be daring and request the tajin rim glasses for a nice contrast.
La Catedral Cafe and Restaurant – An amazing Mexican coffee house tucked in the Mexican neighborhood, Little Village aka La Villita for those who speak Spanish. This spot is my favorite brunch spot for Mexican breakfast items and European inspired Mexican dishes. You will get your waffles, paninis, chilaquiles (best way to describe this is breakfast nachos minus the loads of cheese and with a fried or scramble egg) and luicados (shakes) too. Their coffee is delicious but be warned to order 1 and share with a buddy as their mugs come in out of this world sizes. This brunch spot isn’t a well kept secret as the restaurant appeared in the 2006 movie “Stranger than Fiction” so as one can expect, the wait time for this small coffee house during the weekends can be quite long but certainly worth it. (FYI: I usually always visit during the weekdays to avoid the lines and will still be shocked with how filled the restaurant will be during the week.)
Golden Nugget Pancake House – For an old school dinner style restaurant with delicious food head to the north side of Chicago for this 24 hour, open 365 day dinner chain. Trust when I say that you will get your fix and not be disappointed. Their menu is extensive so even the picky eaters will find something and prices are very economical.
Inspiration Kitchen – This is a great hidden gem for brunch that doubles as a nonprofit organization combating homelessness in Chicago by providing job training and support to homeless people. They classify themselves as contemporary American cuisine but I would say they offer more southern options like “fried green tomatoes and “shrimp and grits” (These fall under my “Must Order” as it’s what I tend to order 90% of the time.) Big plus is that they are a BYOB spot so your brunch can still be boozy if you choose. Tip: Make a 1/2 day out of this and check out the Garfield Park Conservatory which is a short 3 minute walk and free to enter.
Those who know me, know that I am notorious for looking at dessert menus before ordering food to base my food order by what I will eat for dessert or replacing meals with dessert in order to save calories and not feel like I have ate so much. All to say that I am a professional here and my options below are the best of the best.
Original Rainbow Cone – Located in the far south side of Chicago in the Beverly neighborhood and accessible best via uber or car. This is one of the oldest standing ice cream shop in Chicago having opened in 1926 and having one of the most original and most coveted 5 slabs of ice cream on a cone. The combination of flavors is a treat especially for dessert lovers like myself who want all the flavors in one cone. This ice cream parlor and it’s cone has made it on many foodie and travel guides and is a must in my books if you are able to make the trip.
Must Order: The “small” cone isn’t small at all but it is the perfect size to truly enjoy all the flavors and don’t you dare try to omit flavors. This will take away from trying the original rainbow cone the way it was intended to be.
Margie’s Candies – Being established in 1921, Margie’s candies is the second oldest ice cream parlor in Chicago serving sundae’s, shakes and candies. Legends such as mobster Al Capone and the Beatles have delighted themselves here but the best part about this parlor is how this ice cream parlor still has the aesthetics of the way it looked over a century ago with the same booths and decor. Tip: Sundaes are delicious but certainly shareable so don’t get too over zealous by ordering one for each person. #Share.
Artopolis – This Mediterranean cafe in Greek town is another wonderful spot if you have a sweet tooth or looking for strong Mediterranean coffee. Their extensive selection of delicious bakery items will not disappoint.
Additional food to eat while you are here:
- Mexican tamale’s from the women in street corners. Typically sold in the morning and accompanied with “champurrado”, a Mexican thick hot chocolate which is also sold by these carts.
- Continuing with yummy street food, don’t miss snacking on Mexican style corn on the cob. Neighborhoods like Pilsen and Little Village will have plenty of vendors. Add a cup of fruit with chili and a bag of their “chicharrones” with chili sauce for a full and calorie filled meal.
- Taco Bell Cantina – Chicago holds the first boozy Taco Bell restaurant in America. Let me make a BIG disclaimer here, this is not Mexican food, this is just another American fast food restaurant and if you can see it for what it is then the food isn’t half bad. It helps when you have the ability to order alcohol at the same time and that they close late.
- Beatnik is a fabulous option if you really want to roll out the red carpet for your taste buds and eyes. Every item and cocktail I’ve ordered here reminds me how amazing Chicago cuisine can be. A MUST if wanting to treat yourself while here.
Where To Party
Eastroom – Stylish cash-only hangout offers cocktails & brews in a low-lit cozy venue with exposed brick walls.
Chicago Athletic Association – Set in an 1890s Gothic building that once housed an exclusive sportsmen’s club, this chic hotel offers some amazing bars throughout the hotel offering a different taste and vibe so be sure to indulge in some pre-night out beverages here.
Punch House – Hidden basement bar serving up creative & classic punches. Just consider yourself warned that they go down quite smoothly but you’ll certainly feel it the next day if you aren’t too careful.
Harbees Liquor & Tavern – Friendly neighborhood bar that has several brews on tap and a dance floor in a laid–back atmosphere. Best part, it’s BYOF so bring on the food.
Green Mill – Swinging sounds are on tap nightly, from big-name artists to local late-night jam sessions. Shades of Al Capone’s heyday are found in the wall memorabilia as you enter and in the famous booth where he and his henchmen would keep a cautious eye on both doors.
Cabana Club at The Robey Chicago – In an art deco–style former office building dating from 1929, this hotel’s rooftop terrace bar offers sweeping city views.
Blind Barber – A funky, shave-&-a-haircut shop opens its back doors to reveal a ’70s-themed bar with dope DJ sets to match.
Maria’s Packaged Goods & Community Bar – Hybrid liquor store & neighborhood tavern supplying a large rotating menu of rare craft beers.
Longman and Eagle – Hipster spot with modern farm-to-table fare & whiskey & craft cocktails.
The Violet Hour – Rooted in pre-prohibition creative cocktails & small bites define this sophisticated, stylish bar.
Broken Shaker – Located inside of the Freehand hostel in downtown Chicago, this funky space offers mixologist craft cocktails in a hip environment.
Waydown – Stylish rooftop bar for cocktails & bar plates at the Ace hotel has two patios & live music or DJs.
The Darling – The Darling is a bar and restaurant in The West Loop that serves American food and is decorated like an old mansion.
Must Try: Malort shot, drinking a shot of Jeppson’s Malört is a Chicago tradition and a right of passage for any Chicagoan, wanna-be Chicagoan or tourist trying to step up in the Chicago ranks. Go ahead, join the Chicago Club.