Sweet Home Chicago: A Tourist’s Guide to the Windy City

We’ve been meaning to do a post about Chicago for some time now. Not just because we get so many emails & messages from readers traveling to Chicago who want the inside scoop, but also because we both L-O-V-E this place we get to call home.

Now we must preface this by saying, we are not Chicago experts. In fact, we both grew up in a suburb of Chicago…which to a true Chicagoan…means you’re not actually from Chicago. But we’ve been visiting the city ever since we were kids, and now as adults 1 of us lives here, and the other is downtown just about every weekend. So we’re not experts, but we certainly can act as rookie tour guides to our town.

So if you’re planning a trip to The Windy City this should help you fill up your travel to-do list.

When To Visit

There is nothing like summer in Chicago. It is the most wonderful time of the year…by far! Boats are out on the lake, patios open up for happy hour, and locals are so happy to soak up the sunshine. Not to mention there is so much more to do during the summer months, including festivals, concerts, movies in the park, and more. So if you have your pick…come see Chicago in the summer.

The Christmas season is also a phenomenal time to come check out Chi-town. The city is lit with lights and decorated to perfection. Yes it’s cold, but it’s worth it! Get all of your Christmas shopping done on Michigan Avenue, go ice skating in Millenium Park, and sip on hot cocoa as you explore the city.

Fall comes in a close third…followed by the springtime. #sorrySpring

Where to Fly

If you’re flying into town, O’Hare International Airport or Midway Airport will both do the trick. Chicago doesn’t allow Uber drivers to pick anyone up directly from the airport, but there should be plenty of taxis available to drive you where you need to go. If you’re staying in the city, we would not suggest you renting a car because paying for parking at a hotel can be upwards of $50+ per night! You really do NOT need a car if you plan to stay in the city, which bring us to our next topic….

Getting Around Town

Chicago is a biiiiig city, and there’s no way you can explore it all on foot. You can Uber or take a taxi just about everywhere, but public transportation is also an option. Similar to NYC, Chicago has a subway system, but ours is called the “L” (short for “elevated”). It’s a very useful tool to get around the city, especially when you want to avoid traffic. If you’re looking to explore neighborhoods outside of “the loop”, then the train is the most cost effective way to see lots of areas. Plus, it’s inexpensive at $2.25 a ride. And if you don’t want an expensive cab ride to and from the airport…the L is the way to go. Take the orange line to Midway or the blue line to O’Hare and save some serious cash on transportation.

Bonus Points: Take a ride on a water taxi to get around and see the city from a unique point of view!

What to Eat

Chicago has hundreds of fantastic restaurants. Seriously some good eats in this town. There’s no way we could list them all, but here are some places you might want to cross off your Chicago bucket list. We consider them to be touristy spots, but they’re worth a visit at least once!

  • Deep Dish Pizza: Lou Malnati’s, Gino’s East, Giordano’s, or Pizzeria Uno. Everyone has their favorite spot, so hit one up and get ready to eat… a lot of pizza.
  • Portillo’s: Chicago hot dogs, Italian beef sandwiches, and fries. Yum.
  • Garrett’s Popcorn: This is the tourist hot spot for popcorn. There are locations all over and you gotta be sure to get the Chicago mix (cheese & caramel corn combo.) You will have yellow, cheesy fingers but it’s oh so worth it.
  • Doughnut Vault: Get your sugar fix on first thing in the morning with a delicious donut. Make sure you act fast because once the donuts are sold out, this teeny-tiny shop closes for the day (and often times there is a line out the door)! If you’re too late for the doughnut vault, try a doughnut from other local hot spots like Glazed, Stan’s, Infused, fire cakes or do-rite. <– we’re hungry just thinking about these delicious hot spots.
  • Intelligentsia Coffee: Chicago based coffee spot with locations throughout the city.

Again, these are just the list of tourist spots that you may want to check out. You’ll want to do your own research to find the hidden gems of the city for all of your meals. Lots of good food in Chicago…

What to Do

  • Take a picture at “The Bean”: This is the large bean looking statue in Millennium park that’s actually called Cloud Gate. It’s a fun photo op spot. Funny story…one time while walking to work a tourist came up to me and asked where he could find “the large peanut.” I laughed so hard.
  • Buckingham Fountain: This iconic fountain is very close to the Bean, so you can get photos at both spots in about 15 minutes.
  • Go to a Game: Chicago is a sport town, so squeeze in a Bulls, Bears, Blackhawks, White Sox, or Cubs game while you’re in town!
    – Chicago Bears = Soldier’s Field (Museum Campus)
    – Bulls & Blackhawks = United Center (West Loop)
    – White Sox = US Cellular Field (you’ll have to jump on the ‘L’ and head south to 35th street)
    – Cubs = Wrigley Field (old, iconic, charming stadium on the North side, also very accessible by way of the ‘L’)
  • Visit a Museum: Take a few hours and visit one of these…The Art Institute of Chicago, The Field Museum, the Adler Planetarium, or The Shedd Aquarium. (They’re all right by one another, so you could maybe squeeze in 2 in an afternoon!) ** Sometimes teachers get in free so check the websites and call ahead for you teachers on summer vacay!
  • Second City: Buy a ticket to a comedy show at Second City and you may see the next big comedian on-stage. The comedy company has spawned some of the funniest people on TV (Tina Fey, Steve Carell, Stephen Colbert…)
  • Architectural Boat Tour: If the weather is nice this is a MUST. Learn some history about this gorgeous city and take in breathtaking views. Plus, you can grab a cocktail while aboard. You can pick up an architectural boat tour right on Michigan Avenue and the Chicago River.
  • Lakefront: Get your walking shoes on and spend some time exploring the lakefront. An absolute must if you’re visiting in the summer. (Grant Park, Maggie Daley Park for the kids, Buckingham Fountain, Navy Pier, Pritzker Pavilion for free concerts as seen above … all walking distance from the lakefront)
  • Michigan Avenue Shopping: Visit swanky stores (and some affordable ones!) while shopping the “Mag Mile”. You can even catch a horse & buggy ride at night around the Water Tower, which is right on the Mag Mile.
  • State Street: More shopping and home to the original Marshall Fields (now Macy’s). This is where you will find the famous Marshall Field’s clock and if you’re visiting in the winter, you’re bound to see all of the Macy’s windows decorated for the holiday. Grabbing a hot chocolate and looking at the “windows” is an iconic Chicago tradition and one that is bound to get you in the holiday spirit. You’ll also find lots of Garret’s popcorn in this area.
  • Theatre District: There’s no need to go to the Big Apple, you can see some great shows right here in Chicago (and the tickets are probably cheaper!)
  • Hancock Building: Grab a drink at the Signature Room on the 95th floor and take in breathtaking views of the city. The drinks are a tad pricey, but this is a great way to see the views from above at least once. You can also grab a fancy brunch here too.
  • Willis Tower (formerly known as the Sears Tower): You can buy tickets and take a trip up Chicago’s tallest building. Not only will you see the city from above, you can also step out onto a glass sky deck which allows you to look straight down from 99 floors up. (NOT recommended for those who have a fear of heights!!) #yikes
  • Navy Pier: This is actually the number one tourist attraction in the midwest?! A family friendly pier with souvenir shopping, activities for the kids, boat rides, home of Chicago’s ferris wheel, lots of food, music and fun. Also a great place to catch fireworks in the summer on Wednesday and Saturday nights.

So it looks like you’re going to be very busy on your next trip to Chicago! Heck, we are only skimming the surface and hope to write more Chicago-themed posts in the future. In the meantime, we hope you come and see all that our sweet home Chicago has to offer.


  • Summer Hogan

    So fun! I love Chicago but it’s been a long time! I may have to venture back πŸ™‚

  • Heather

    As someone that grew up in the burbs of Chicago, I will second your notion that spring is NOT the time to visit. I try to get back up there every year (my dad and his side still live there) and last spring we went up for my cousin’s wedding in May. I took my husband to a Cubs game so he could see Wrigley and it snowed! It was a miserable snow too. Instead of beer guys going through the aisles, they had hot chocolate guys! Geesh.

    What a great list though! Makes me want to get back home before summer ends!

    • We are laughing out loud at this story, only because it’s all too familiar. Thanks for sharing, Heather!

  • Oh my goodness, that is hilarious and AWESOME!! Thanks for sharing these extra tips… we hope to do a Christmas in Chicago post in the winter too, so we’ll have to add these tips. Thanks Aimee!!

  • Alice H

    Great list! We have some great food trucks here in the city too – I work in Hyde Park so I’ve been able to sample a few. Also, instead of going to the touristy restaurants, ask the concierge for some neighborhood recommendations. I’ve had some of the best meals in Chicago in places that weren’t packed with tourists. Also Segways or the Divvy bikes are also another great way to see the city. There are also small museums throughout the city as well – at University of Chicago there is the SMART Museum as well as the Oriental Institute. We also love going to the Harold Washington Museum – very cool place to visit as well.

    • We couldn’t agree more– you can’t go wrong with local restaurants in neighborhoods throughout the city. So many hidden gems!

  • Lara Gephart

    CRAVING Portillos! I’m headed up that way for work next week and I’m already petitioning to stop at Portillos in Bolingbrook on the way home πŸ™‚ Another fun place to eat (if you have a car) is Super Dawg. They have giant Tarzan and Jane hot dogs on the roof and it’s like a 50’s drive up diner. I wish my husband liked hot dogs because we would be there all the time!

    And I totally agree Chicago in the summer is far superior to all other seasons. And spring = the worst. Just when you think the snow is done and warm weather is here forever, NOPE. At least in the winter, you know what to expect.

  • Trang

    Wow, this was a challenge to post for you because where do you even start with listing foods to eat while in Chicago? That is the biggest challenge for me when I come into town. I have all the ‘to do’s’, but unfortunately, never cover 1/2 of the list because there are other unexpected fun things to do, eat, and check out. In Indian town, I have this favorite Indian food restaurant that is amazing, but I’ve yet to return since going there 2 years ago. I keep saying this upcoming trip in August will be the return to it! So many celebrity chefs have restaurants in Chicago. It’s difficult to decide which one to go to and you have to make reservations way in advance, but so worth it. My favorite so far was The Girl & the Goat – phenomenal place!
    Being a craft beer lover, your town has developed some tasty brews! My favorite is Half Acre, but I also like Revolution. One of the best experiences while in Chicago 2 summers ago was doing a craft brew tour (there are 2 to choose from). I got to explore cool neighborhoods like Bucktown and Wicker Park much better. Oh, that’s another thing to add to the list, each neighborhood has it’s own charm and fun things to explore – especially in the summer when they host festivals.
    I’m in the air about whether spring or winter is the worst time to visit Chicago. I once had much difficulty getting into the city because of a flood. It took way longer than it normally does because I had to go around the closed section of the highway. And winter – well, I’m just a sissy. I can’t handle cold too well and with the wind there – whew! I once took the Megabus into Chicago in January and thank goodness I didn’t have to maneuver through all that snow! I’d be a nervous wreck.
    Sorry for the long message, but I just love your town. I always say that if I win the lottery, I’m so getting a condo there!

    • Amanda Scott

      Girl & the Goat is amazing! We just got a few small dishes to share to save money (a great trick for saving money but experiencing the best restaurants in Chicago). The goat carpaccio still makes me drool. I’ve remade a few of the dishes at home since (like an amazing tomato bread with chive cream cheese), it’s a fun way to remember your trip & save money.

    • Trang

      what is this tomato bread with chive cream cheese you speak of? Recipe please!

    • Amanda Scott

      It was a while ago, but it was a basic round of bread made with what I think was very finely chopped tomato (a few small pieces, but nothing my tomato-hating boyfriend couldn’t ignore), so I actually shredded a small tomato & added it to a bread dough – a little corn meal at the bottom adds great crunch. It came with tomato oil we didn’t remake, and it was spring onion cream cheese (just fold in finely chopped spring onions into cream cheese and let it hang in the fridge for a bit). It was last summer so it was wonderfully seasonal. I should make it again!

    • Love this idea!!

    • You are so sweet!! And yes, Chicago is pretty fabulous… isn’t it?! Thanks for sharing these tips!!

  • Amanda Scott

    I’ll add that you can take the Blue Line from O’Hare (great if you’re staying anywhere near the loop, but a trek if you’re going to the far North Side). If you go to Chicago during the warm months be sure to check out all the free activities – concerts at Millennium park, movies at various parks, and especially neighborhood festivals. Wicker Park Fest is this weekend! If you’re going to a very busy area, definitely take public transport. You don’t want your Chicago visit to be 50% traffic. Also check out all the Chicago Breweries – Goose Island, Pipeworks, Revolution, Half Acre, Dryhop (amazing food).

    If you can visit more than once or have a longer visit you should definitely visit the various neighborhoods. I LOVE Wicker Park & Bucktown, there’s also Pilsen, Lakeview, Greektown, Ukranian Villiage, Old Town, Hyde Park, Wrigleyville, Logan Square (lots of great food), River North, of course Lincoln Park (visit the zoo, park, & Lily Pond, and walk around to see the amazing homes of E Lincoln Park you could never afford), Boystown, Lincoln Square (small up n coming), Edgewater & Chinatown (get some authentic Dim Sum). Check out the beaches during the summer! The parks next to the lake are really freaking beautiful (get a Divvy bike and go on Lake Shore trail, just be sure not to accidentally go on the highway, which does happen. ha).

    What I would say is key – explore & don’t go to chains (at least not nationwide chains – def do portillos) and wear comfy shoes so you aren’t feeling limited. Don’t think you have to spend a lot of money in Chicago. Do free activities, have downtime at local bar patios, take public transport. Also: weekday cubs games are where it’s at (cheapy cheap). Finally, be aware of travel times to places – distance is different in the city vs suburbs. Unless you stay in one neighborhood you will spend more time than expected traveling.

    PS If you are dong a fancy weekend check out afternoon tea at the Drake. It’s the stuff dreams are made of.

    • Trang

      Girl, you are woman after my own hear with all the brewery listings and neighborhoods. I so love all of what you listed!
      I’m going up there in a couple of weekends for Market Days in Boystown (my friend lives there). So looking forward to drinks at Elixer – best mixologists. I think hubby and I want to check out more of Logan Square this time too. There just simply is not enough time to do all the things and eat all the diverse offerings I want while I’m there each time.
      About replicating the dishes you had at Girl & the Goat – I did the same thing. For the next week after I got back from Chicago, I was obsessed with perfecting crumpets. That was one of the small appetizer dishes we got. I even watched videos of Stephanie making some of her small dishes. Yeah, I’m a bit OCD when it comes to food and eating. πŸ™‚

    • Trang – Fantastic tips! I am visiting Chicago.

    • You are AMAZING…. and OMG, thank you so much for adding all of these great tips!! Super resourceful and SPOT ON!

  • Perfect timing! πŸ˜‰
    I’ve never been to Chicago as an adult before (ie, figuring out all my own plans & transportation) but I’m looking forward to a trip in December!
    Visiting from LorimerLiving.Com
    XO, Jaclyn

  • My husband surprised me with a surprise weekend in Chicago last summer for my birthday and I had so much fun! We flew up from STL into Midway and got a 3 day pass for the public transit, which was awesome. I made him get up at 6 AM on a Saturday so we could see some of the sights w/o all of the tourists. Being basically the only people at the Bean was amazing! We ran the lake front trail and down the Navy pier before winding our way back to our hotel.

    We bar hopped in Wicker Park, saw a Cubs game, did the Hancock Tower (no crowds Sunday mornings!), did the nighttime architectural river cruise and met up with some friends for brunch at Beatrix. We also stopped into The Dawson for a couple of drinks and really liked it!

    • Wow, your trip sounds like it was pretty amazing!! What a great husband you have =)

  • Amanda Scott

    Also a note: as of august 1 2015 Chicago is disallowing distribution of single use bags, so bring some reusable bags!

  • Colleen Bansley

    If you come to visit Chicago during the holiday season Tea at the Drake, Four Seasons or The Peninsula is a great tradition especially if you have little girls or are with your girlfriends! The decorations are beautiful and you get great little sandwiches and sweets and can order champagne or wine. Surprisingly it is not that expensive! Also catch a show at the theatre. You don’t have to spend a ton of money to go to one of the big theaters in the theatre district. There are some small theaters that feature great shows, i,e., Million Dollar Quartet at the Apollo Theater, and others. Also one of my personal faves as a city dweller is treating myself and my girlfriends to lunch at RL! The lobster bisque is beyond delish. Pricey menu, but it is so worth it and a special experience! Oh and you can’t miss the Christmas decorations at Butch McGuire’s on Division- amazing! Super fun place to go for lunch or late night. We used to go every Christmas Eve with my family and it is a great tradition- great food, amazing decorations, kid friendly (yes they have bar height table hi chairs)!

    • Thank you so much for adding these tips, Colleen! We appreciate this feedback and all of these are SPOT ON! We will have to add these to our future Christmas in Chicago post too. You are amazing!

  • This is awesome! I’m in Indiana, within a few hours of Chicago but I haven’t been there in over 10 years! Keep thinking we should go back some day! This is a great start of places to see/do! Thanks!

    • Diana you’ve gotta get to Chicago…you’re our neighbor! We think 10 years is too long! Come visit πŸ™‚

    • Hopefully soon-ish!!

  • Michelle Conn

    Billy Goats!!!!!!

    We live less than an hour away and make frequent day trips up. I’m always sad if we don’t eat at Billy Goats or Ginos East. We must stop at one on every visit!

    The boat tour through the locks and out onto the lake is also fantastic. It teaches you a lot of Chicago history.

    Whenever we take friends or out of towners to the city we always drive through and show them the different buildings and sites where movies have been shot.

    So much to do there!


  • Elizabeth Cagle

    Does anyone know the best transportation method from the Train station to the Drake hotel? We are visiting in August for a girls trip.

    • Which train station?

    • Elizabeth Cagle

      Amtrak Chicago Union Train Station.

    • Definitely too far to walk, especially with luggage. Your best bet is to hop in an Uber or a taxi. Shouldn’t be hard to get one in that area! Have fun.

    • Elizabeth Cagle

      Thank you!

  • Leentje

    Nice piece! Check http://www.chica-go.us for more πŸ™‚