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 love 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 it’s 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

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.

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.

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.

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.

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).

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.

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!

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.

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”.

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.

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.

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.

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.

Found this pin useful? Pin it for later!