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How to Experience Chicago in Two Days

When it comes to U.S. cities, I'm always going to be a bit bias to my hometown, New York. C'mon, Frank Sinatra even got famous for singing all about it. But Sinatra also had another song called "Chicago", a city he regularly discussed his adoration for. And considering how difficult it is to go a day in Chicago without hearing him blaring over the radio, I think it's safe to say Chicago loved him back.

When it comes to U.S. cities, I’m always going to be a bit bias to my hometown, New York. Between the constant movement, the air of ambition, and the best bagels and pizza you’ll ever have the pleasure of eating after a long night out, it’s hard not to be. C’mon, Frank Sinatra even got famous for singing all about it.

But Sinatra also had another song called “Chicago”, a city he regularly discussed his adoration for. And considering how difficult it is to go a day in Chicago without hearing him blaring over the radio, I think it’s safe to say Chicago loved him back. And just like his song “Chicago”, which was simple and catchy, this city will have you relishing in its urban simplicity and humming along as you stroll down State Street. I’ve been to a few cities, but Chicago is one I could see myself going back to again and again – hopefully for longer than a weekend next time.

But luckily, due to the compact size and design, you can still experience a whole lot of Chicago in just a couple of days

DAY 1:

Pre-Breakfast at Goddess & the Baker

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Goddess and the Baker

Goddess & the Baker had been recommended to us by quite a few people, and while the breakfast menu didn’t call out to me, their baked goods definitely did. Of their most popular offerings, one is their rainbow cake, which you may have scrolled passed on your Instagram feed one or two times. Since we had a half hour to kill before our breakfast spot of choice opened up, we decided “why not” and decided to get a slice of that tempting rainbow cake at 9 am.

Let me start off by saying that other than Dominican cake (#DominicanPride), I’m not really a cake person. But this cake was like no other I have ever tried. I’m not sure how they were able to make this as moist as they did or what flavorings (but I’m thinking extra vanilla) they added into their mix, but we wanted to savor every single bite of it. The cake is also topped with almost whipped-cream style frosting that wasn’t overbearingly sweet like many others.

I literally did a Google search to see if it was possible to have one of their cakes delivered to New York, if you need it’s perfection put into context.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Goddess and the Baker


Grab Brunch at the Gage

Any restaurant with an Irish breakfast and corned beef hash on the menu is a place I’d like to be. In case you’re wondering, I went with the latter. The Gage is an American restaurant with slight Irish undertones and sits right across the street from Millennium Park, providing a tourist’s perfect view if you choose to eat outside.

We did and ended up regretting it once the heat spiked but despite being slightly uncomfortable, my boyfriend said he’d dream about his side of Gage potatoes and I’d rank my corned beef hash in the top three I’ve ever had.

Pro Tip: Winters in Chicago may be notoriously cold, but their summer heat can be unbearable. We went over Memorial Day weekend and were hit with 92 degree weather both days, so make sure to check the forecast beforehand and be aware that Chicago’s temperatures tend to be a bit extreme.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | The Gage

Take a  Walk Through Millennium Park

They say you can’t leave Millennium Park without taking a mirror picture in Cloud Gate, also known as the Bean – but I found the Bean to be way less worth dodging a crowd for than waiting ten minutes to watch random faces “spit” water at Crowne Fountain.

I know schedules can be tight, and you may have an urge to take that prized photo of “the bean” and run, but there are so many hidden gems of Millennial Park. During our stroll we ended up coming across several small gardens we had no idea were there.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Crowne Fountain in Millennium Park

Spend a Few Hours at the Field Museum

We had a tough time choosing between the Field Museum and the Museum of Science and Industry, but considering that this museum is much closer proximity to where we were spending out day, and online reviews seemed to lean towards the Field Museum, it didn’t take us long to make a decision.

Admission ranges from $24-$38 depending on the ticket you choose, though the middle option, which includes General Admission and admission to one 3D movie seemed perfect for us. But honestly, the museum is so expansive, you’d probably have a great experience with General Admission alone.

You’re greeted at the Field Museum by Sue, a 67-million year old T-rex. From there you can visit an ecolodge to an Egyptian pyramid.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | The Field Museum

Grab a Classic Chicago Style Hot Dog

We spent many a Google search trying to find out where to get the best hot dog in Chicago – in the end, just like in New York, the best hot dogs can usually be found at a random hot dog stand. Lucky for us, we spotted a hot dog stand right outside of the Field Museum almost as if it were waiting for us. This stand not only offered classic hot dogs, but vegetarian and turkey options as well, which is great for people who enjoy that but I already knew I was getting a classic with all the Chicago goodness (a.k.a pickle spear, relish, onions, and mustard).

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Chicago Style Hot Dog | Chicago Eats

Let Out Your Inner Athlete at the Chicago Sports Museum

The Chicago Sports Museum is located inside the Water Tower Place mall along the Magnificent Mile with a price of admission of only $10! On top of that, it’s one of the smaller, lesser known museums so we almost had the entire place to ourselves. The concept is pretty similar to that of the NFL Experience in Times Square, combining nostalgic sports adverts and equipment with interactive experiences. Guests can compete as a goalie with Blackhawks, jump on the court with Bulls, or stay behind the scenes desk recreated to look like that of the late Harry Caray’s – an American sports broadcaster.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Chicago Sports Museum

Have an Authentic Italian Meal at Rosebud on Rush

Let me start off by saying that Rosebud on Rush was a long-time favorite of stars like Frank Sinatra, Tony Bennet, and Robert Redford, so if you’re looking to follow in the footsteps of legends, add this spot to your list. Second, the atmosphere makes you feel as if you’ve been transported back to Chicago in the 1940’s. Finally, there food was so good that I literally texted all of my closest friends back home in New York, just to tell them that I finally found a city to compete. My pappardelle was the perfect texture and was cooked to perfection (and in-house that very day). Should I go back to Chicago, this place will always be in the itinerary. And to think, we only ate here because the line at Giordano’s was around the block; so thankful for that!

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Rosebud on Rush | Chicago Eats

Wrap Up Your Day with the Navy Pier Fireworks

I’m a Disney World fanatic, meaning most firework shows do not reach my standards and the Navy Pier Fireworks are no exception. However, as a relaxing way to wrap up a jam-packed day with Lake Michigan as the backdrop in one direction and the Centennial Wheel as the backdrop in another, it’s a fun add-on. Unfortunately we didn’t have time this day to actually enjoy the Navy Pier, but we were glad to not have missed visiting entirely.

Pro Tip: Should you decide to end your night at the Navy Pier, analyze your transportation options fully before going. By the end of the firework display, the amount of people leaving was so many that we, and many others, experienced almost 45 minute “searching for a driver” Uber and Lyft waits. Chicago has a decent subway system, but most stops actually leave you a few blocks (or quite a distance) from the main attractions, including the Navy Pier, so public transportation wasn’t an option. Regular cabs were even up-charging up to $40 for a not-worth-40-bucks ride to the train station. Eventually, we decided to walk a few blocks and came across the most awesome cab driver who charged us just $10 to get to the station, and from there it was just a 25 minute ride to our hotel on the blue line.

DAY 2:

Spend a Morning at the Adler Planetarium

There are three admission options for the Adler Planetarium: General Admission, which gives you access to the museum only; the Basic Pass, which gives you access to the museum and one sky show; and the Anytime All Access Pass, which gives you access to the museum on any date of your choosing, one sky show, and access to the Historic Atwood Sphere Experience – but most of the salespeople will tell you that the Basic Pass provides enough for one day.

With this pass we were able to spend a couple of hours scoping out each unique exhibit, ranging from topics like Astronomy in Culture and A Walk Through Space and Time, as well as one interactive star show in the dome-shaped planetarium.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Adler Planetarium

Take in the View of Lake Michigan

A few feet from the Adler Planetarium you’ll find you a short stairway leading your directly towards Lake Michigan, which provides a relaxing and scenic view after a few hours roaming the museum. On a beautiful day like ours, it almost felt as if we were relaxing along the coast in California, with the blue water and Chicago skyline in the background. If you remember your bathing suit, you can even hop in for a quick dip along this “tar beach”.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Lake Michigan

Grab a Churro at La Bodega

If you’re thinking that this spot sounds like a hipster bodega, you are absolutely correct; but I’m in no position to judge a shop that focuses solely on coffee, hot sauce, tacos, and various flavored churros. Yes, it is as awesome as it sounds, plus there’s an assortment of piñatas hanging from the ceiling.

We ended up getting a couple of coffees, as well as a Red Velvet churro and a Fruity Pebbles churro. While the Red Velvet option was good, Fruity Pebbles was the real winner due to the creamy filling. We didn’t grab any tacos on this round, but we did get to enjoy the delicious aroma of some being cooked in the back, and it was almost enough to make us consider a pre-lunch lunch.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | La Bodega | Chicago Eats

Stroll Along Riverwalk

While Memorial Day weekend meant the river was packed with private yachts (apparently everyone in Chicago owns one?) and tour cruises, we couldn’t leave without checking out one of Chicago’s staple locations. We actually stood along the river, sipping what remained of our coffees for a good half hour just taking in the scene – and also questioning how such an urban city managed to keep their waterways looking so clean.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Chicago Riverwalk

Get a Cliché Snap of the Chicago Theater

The Chicago Theater is not only one of the most legendary venues in the city, but it’s also a widely popular landmark. The theater was one of the most visited movie theaters from 1925-1940 and post-restoration, now serves as a venue for concerts and tours.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Chicago Theater

Grab a Quick and Delicious Lunch from Nando’s

If you’re from Chicago, Washington D.C., or parts of Maryland, you may have always known about the culinary magic that is Nando’s. If you’re not, you may have had your first experience with the not-so-fast fast food spot abroad in the U.K. We had Nando’s for the first time in Ireland where we willingly ate it, and I kid you not, three times in seven days. Nando’s centers around chicken and Mozambican-Portuguese flavors, but unlike other “fast-food” chicken spots, this chicken is grilled fresh on a grill right in front of you after it’s dipped in one of their several tasty marinades. In fact, a majority of their sides are even completely healthy. Okay, maybe not the garlic bread but it’s made on Portuguese bread, so I’d suggest saying “to heck with it” and ordering it anyway.


Catch a Cubs Game at Wrigley Field

Whether you’re a die-hard baseball fan or someone who just enjoys cracker jacks and the roar of the crowd, you can’t miss out on the opportunity to catch a Cubs game if you’re in Chicago during the season. We were able to get two 400-level seats (a.k.a, the best seats anyway) for about $32 each on Stubhub, but they weren’t going for much more on the official Wrigley site.

The appeal of Wrigley is it’s old-school design, which provides an entirely different feel than fields like Yankee Stadium. While the tech leaves something to be desired (we couldn’t hear a thing broadcasted over the speakers), it’s worth visiting for the nostalgia value alone.

Pro Tip: Don’t splurge on overpriced Cubs swag at Wrigley Field. There’s a sports store right across the street that had a bargain bin of $10 Cubs t-shirts that served us just as well.

How to Experience Chicago in Two Days | Weekend Trips | US Travel | Chicago, Illinois | AGBHOW | | Wrigley Field | Chicago Cubs


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42 comments on “How to Experience Chicago in Two Days

  1. This is such an awesome and jam-packed itinerary – defs saving it for next time I am there!


  2. kindleandkompass

    So many things to do that we did not know about..thanks for sharing!! 🙂


  3. I have been wanting to to to Chicago for a while, and this makes me want to go even more! My husband is a huge baseball fan, so thanks for the tip about the store across the street from Wrigley Field.


  4. Give me allll the Chicago dogs! 😛 I visited when it was a very chilly March and would love to go back in warmer weather!


  5. This is perfect! I am giddy since you recommended Nando’s! Not going to believe it but for lunch, I had chicken with one of Nando’s sauces. We do not have a restaurant in LA but we got several sauces at World Market. We were recently in London and ate at Nando’s like three times. So, that is one more reason to visit Chicago (like there are not enough).


    • Our local supermarket actually stocks three of the Nando’s sauces too so we stock up for when we’re home! It’s definitely underrated.


  6. Chicago is my hometown but I don’t own a yacht, lol! I love that you included “pre-breakfast” – that is my kind of travel! I’m going to pin this for the next time I go home (moved away last year) because there are places on here I haven’t tried that sound amazing! Thanks!


  7. The food look so good! Haha I would go to Chicago just to eat! One of the best cities in USA 😛


    • Wouldn’t blame you! Already planning a trip back in the future because there are so many places we didn’t get to eat at, haha!


  8. This is so great! I read this after lunch but hearing about the gorgepus churros and that epic hot dog, I am definitely hungry again;) thanks also for pointing out the Adler planetarium and the Field Museum, I am a nerdy traveler, so those are right up my alley!


  9. I am intrigued by the cake. I’m also not a cake person, so a cake that would induce a non-cake person to such lengths, makes me curious indeed!


  10. Wow this was very detailed, and your tips are very helpful. Hope I could visit Chicago, looks like you had a great time.


  11. I LOVE Chicago but have only ever been for work – so I’ve missed a lot of stuff! I would love to go back for an actual visit…. and I would 100% need to eat at Rosebud on Rush!


  12. I’ve never visited this US city. I love learning about city brunch spots so I can make a note about it for future visits! That Wrigley field sign is iconic as I’ve seen it on many US network TV shows as a child.


  13. Haha, love that you chose to eat a rainbow cake 9 in the morning, that’s something I could do too! And this definentely made me wanna go to Chicago more, mostly to go on a eating fest with churros and hot dogs 😉

    PS. I love New York style pizza


  14. Michelle

    OK, the foodie in me wants to book a plane ticket right now just to grab some of that cake! Seriously! My husband has family in Chicago-surely they would let me bunk up for a night or two. LOL! Thanks for the great tips and recommendations. I will be saving your post for future reference!


  15. I can’t believe you spent all that time in Chicago and didn’t even try Chicago-style pizza! You seemed to have packed in lot of other stuff though. There are so many amazing food options in the city.


  16. Great tips, especially the one about the Cubs merchandise! I went to Chicago many years ago with my dad and loved it. I was obsessed with Frank Lloyd Wright at the time, so as you can imagine, I was in heaven! Would love to return some day 🙂


  17. Mama Travels Earth

    Great tips – especially the food ones!! Love the look of that Chicago hot dog. I’ve never been to New York or Chicago but it’s been a long dream of mine!


  18. Amy Dodd

    Oh my goodness, the food!! I was looking at the cake and thought it couldn’t get better, but those churros look amazing! I didn’t know there was so much delicious food besides the chicago dog..


  19. The baked goods and churros look amazing! I have such a sweet tooth haha. I’m planning on visiting Chicago next year so I’ll definitely be making a pit stop to these places. Thanks for the tips!


  20. I’m not a fan of rushing through a city but I have to because I’m a worker drone, so thanks for this amazingly detailed itinerary. Those pastries look delicious and who doesn’t crave dessert for breakfast!


  21. I have been considering going to Chicago just for a weekend or a long weekend. There’s a lot to do there wow! That cake and those churros look so amazing. They might even be worth the trip just for them. Thanks for sharing your itinerary, it gave me a lot of ideas for a future trip.


  22. I went to Chicago once when I was in middle school but I want to follow your itinerary and visit as an adult. I love that if I want to eat cake before breakfast, I can! and that hotdog – looks like heavennnnnnn!


  23. Zoe | Together In Transit

    You had me craving cake right at the start of your post! YUM! I had to the chance to visit US last year but unfortunately not Chicago, an excuse to go back eh. Great read!


  24. savvydispatches

    I’ve always wanted to visit Chicago but never had much time on my hands for a trip. I’m so glad to see that so many iconic things can be fit into just 2 days. Thanks for sharing!


  25. Lori Tripoli

    I am in Chicago fairly often for work, but I had never heard of the Chicago Sports Museum. I will definitely be taking the kids to visit this one the next time I am in town! Great list of things to do in Chicago in just a couple of days.


  26. I’ve only been to Chicago once, but I really loved it!! It’s so pretty there and definitely a foodie city!


  27. Okay, so you had me with all that food! You managed to find soooo many blooming tasty-looking things to munch on in Chicago! I feel like if I ever visit, I’d want to try all of that, and I’m not totally convinced I can fit it all in my belly (but I’d totally try!)

    The museums all looks fun too, but it’s the views along Lake Michigan and the rivers that are calling to me. I’ve love to just wander along and take in the views.


  28. thegetawayjournals

    Yes! Yes! Yes! Everything on this list! I absolutely love Chicago. Just not in the winter lol


  29. I have been wanting to go to Chicago, ever since the eponymous movie mesmerized me! The windy city, here I come to unravel your secrets!


  30. Pingback: My Year in Review: The Outcome of my 2018 New Year Resolution | A GREAT BIG HUNK OF WORLD

  31. So fun! I haven’t been to Chicago since I was a little kid, so I don’t remember it much. But I think it’s a must-see destination for anyone wanting to experience the great US cities.


  32. I love the way you write and I love the way you food. I was also in Chicago for MDW and loved it! I’m pretty upset that we didn’t visit so many foodie places because I had no idea that these existed until I read your post! The churros at La Bodega are a MUST next time I go back! After reading your description of Rosebud on Rush…as a New Yorker and Italian I feel like I should go to jail for not visiting or knowing about it? I’m so there next time I go back! Excellent write up!


  33. Wow lots to do in Chicago! Seems like a real foodie place and I also like theres a lot of museums and galleries. I’ll be putting this on my list 🙂


  34. We were *just* in Chicago last week and did some of these recommendations! I love the Field Museum, but we didn’t make it to the Planetarium this time. Dang! There’s always next time!


  35. Super itinerary! I’ve never been to Chicago but it’s on my list, as I heard great things about it. I can understand why now, there are so many interesting things to do and lots of fantastic eateries (that rainbow cake is to die for!). I’d surely visit the Adler planetarium and the Field Museum,I love checking out museums!


  36. Black Girl with a Suitcase

    Love the cake for breakfast/ pre-breakfast! Will definitely be adding all of this food suggestions to my list for my next trip to Chicago.


  37. Michelle

    Chicago looks so fun. I love how you focused a lot on food in this post. That is one of the best parts of traveling in my opinion. I have to come just to get a slice of that cake!


  38. What a packed trip! I lived in Chicago for about 5 years and I *still* never got around to a few of the things on this list. Kudos to you for making the rounds– and trying out an impressive chunk of Chicago restaurants.


  39. “Their summer heat can be unbearable” – YES! The first time I was in Chicago it was well over 100 and the streets caved in because they were melting! But I can’t help but absolutely love Chicago. One of my favorite cities!


  40. I used to live in Washington DC so I’m familiar with Namdos but the last time I ate it was in South Africa 🇿🇦 of all places. I love rainbow 🌈 cake so I’m sure it was great. I’ve been to Chicago but I was there volunteering over spring break so I didn’t get the chance to explore! Hope to go back and experience things like a cubs game


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