Much like most of my other travel guides, this one begins with a cheap flight.
Poking around Google Flights one evening (as I’m often prone to do after a glass of wine…) revealed an inexpensive roundtrip flight from Greensboro to O’Hare – departing early one Saturday morning and returning late the following evening.
Driving to another city’s airport to save hundreds on flight costs isn’t new to me – it was something I was used to doing every time I flew while living in Florida – but I had some hesitations about visiting Chicago in March.
Portions of this trip were hosted by some of the businesses or destinations mentioned, but as always, all opinions are my own. This post contains affiliate links in lieu of advertisements to offset the costs of running this blog.
Despite having just returned from a chilly trip to New York City, I understand that a Midwest winter is unlike anything else (even though our trip technically occurred just after the start of spring). But knowing I’ve made strides to bulk up my winter wear over the past few years, I decided not to let a silly little thing like freezing temps keep me home and set about planning a trip to a city I hadn’t had the chance to visit in nearly eight years: Chicago
ABOUT CHICAGO
Chicago goes by many nicknames – the Windy City, Chi-Town, the City of Big Shoulders, and the Second City are just a few – but it derives its official name from an Indigenous word meaning Stinky Onion.
Well, I personally don’t like onions – but I do love visiting Chicago.
Chicago, like its peer and frequent rival, New York, is a city that is tailor-made for tourism. With world-class restaurants, over sixty museums, and a public transit system that is both easy to use and cost-efficient, Chicago is always worth a visit.
A large, sprawling city on the edge of Lake Michigan, the city is divided up into 77 community areas – each with its own personality and more-or-less centered around The Loop. Here is where all of CTA’s rail lines (or the “L” – short for elevated trains) converge.
Chicago is so much more than its downtown core, but with just 36 hours in the city, I decided it was wise to spend our time all in one place (commuting around to different neighborhoods soaks up valuable travel time, after all!). Today I’m sharing my guide to the best things to see and do (and eat!) in The Loop, West Loop, and River North – or the areas most would consider downtown. But before we jump into the guide, here are five fun facts to get you acquainted with the city quickly:
Five Things You May Not Know About Chicago
- The Chicago Fire of 1871 might just be the most well-known fire in U.S. history, but you might not know that the Chicago Fire Academy is now housed at the fire’s ignition point.
- The famed American roadway Route 66 begins in Chicago (unless you’re starting on the other end, in L.A.!) – you can find the route marker near the main entrance to the Art Institute of Chicago.
- The Chicago River is the only river in the world that has been reversed to run backward. Instead of running toward Lake Michigan, it now runs away from it.
- The Centennial Wheel at Navy Pier is now an iconic part of the Chicago skyline, but its importance to the city runs deeper than just sheer thrills. When Chicago hosted the World’s Fair in 1893, the Ferris wheel was the centerpiece of the exhibition – and the very first one.
- Commercial rent for properties along The Magnificent Mile (a 13-block portion of Michigan Avenue with hundreds of luxury retailers) is currently the third-highest in the nation – after Fifth Avenue in NYC and Rodeo Drive in Beverly Hills.
Now, let’s go visit!
THINGS TO DO IN CHICAGO
Arts, culture, sports - Chicago has it all. With such a short time in the city, it's best to find a unique way to get acquainted with the city's layout and to check out its finest possessions.
Wendella Tours & Cruises’ Chicago River Architecture Tour
Wendella Tours & Cruises | 400 N Michigan Ave, Chicago, IL 60611
Wendella Tours & Cruises bills itself as Chicago’s Original Architecture Tour® because, well, it is. Since 1935 the tour operator has been shuttling locals and visitors alike up and down the Chicago River, offering the most incredible perspective on the city’s renowned architectural marvels.
While you can get some sense of the scale and details of Chicago’s architecture from the street level, it doesn’t compare to the clear view only available from the water. And, of course, a guide provides invaluable context to what you’re currently viewing.
The 90-Minute Chicago River Architecture Tour is the perfect introduction to the city’s layout and history, and tours are typically available from morning until evening year-round. Purchase your tickets online to save time, and arrive early for the best seat selection. There’s not a bad seat onboard, but in my opinion, the front right offers the best views.
After a brief introduction and safety presentation, you’ll start making your way down the Chicago River! Our guide was engaging and knowledgeable, sharing each building’s story as it came into view. Properly bundled to fight the chill, we remained outside on the top deck for the majority of the ride – but even if we decided to pop down to the bar to grab a drink or a snack from the full-service bar, speakers are mounted throughout the vessel for an uninterrupted tour experience.
I won’t spoil all that we learned from our guide because I want to make sure you add this essential Chicago attraction to your list. For a quick weekend getaway, I know that it can be difficult to commit a full ninety minutes to any singular stop on your itinerary; for those extra short on time, Wendella offers a condensed 45-minute tour in the evenings.
—
Art Institute of Chicago
Art Institute of Chicago | 111 S Michigan Ave, Chicago, IL 60603
Some of the most iconic works of art can be found at the Art Institute of Chicago. Like many museums in its class, it is simply too vast to be fully appreciated in just a day – and with only 36 hours in the city, that shortens a visitor’s attempts even further. Thankfully, the museum website offers a helpful database of its collection so you can map out your favorites in advance – and there is even a “What to see in an hour” section for those who are unsure of where to start. Do make sure to linger awhile in the Miniatures collection for me (it’s my favorite!).
Buy tickets online to save time and skip the queue – although I will note that the ticket line was significantly shorter than the coat check line (a must-visit portion of the museum when the temperature hovers around the freezing mark!). It is also helpful to time your visit wisely if you can. Arriving earlier in the day will give you better chances of receiving timed tickets for any popular rotating exhibits, if necessary.
This visit coincided with the display of Salvador Dalí: The Image Disappears, and obtaining the (free) tickets for the exhibit was quite competitive. Thankfully, we made it in – a great opportunity to revisit some of the artist’s works. On a cold, rainy day the museum was quite crowded (it is the perfect rainy day activity, after all!), and I should note that there was never much time to oneself with any particular work. Any hopes of recreating the iconic scenes from Ferris Bueller’s Day Off are best left in your dreams (or perhaps, on a weekday).
—
Cloud Gate (a.k.a. The Bean)
Cloud Gate | 201 E Randolph St, Chicago, IL 60602
A stop at Cloud Gate (a.k.a. The Bean) feels like such an iconic part of the Chicago visitor experience that it’s hard to believe it was only installed in 2004. There’s no denying how mesmerizing the reflective sculpture is; the city is reflected so beautifully in the art piece, and there’s something so fascinating about studying the way your reflection moves with you as you explore the curves of it.
Despite being practically made for Instagram (even before Instagram was a thing), it makes for a frustrating subject. It’s nearly impossible to photograph well, because not only will your camera always be in the reflection, but there will always be people around, too. Snap a few anyway, and enjoy a bit of people-watching in Millennium Park.
—
The Signature Lounge at the 96th
The Signature Lounge at the 96th | now closed
You could spend $30 per person for general admission to 360 CHICAGO – or you could head two more floors up for a drink at The Signature Lounge at the 96th (now closed). Entry to the lounge is first-come, first-served, so arrive at least forty minutes before sunset to make sure you can get the best views of the city (before and after sunset). I recommend ordering a glass of beer or wine rather than a cocktail as my drink was… not great. Thankfully, the view more than made up for it.
CHICAGO FOOD + DRINK
I'm just going to say it: you can't eat your way through Chicago in a weekend. When traveling to a new city, it's best to plan a mix of local favorites and stellar standouts.
Tzuco
Tzuco | 720 N State St, Chicago, IL 60654
It seems I have a thing for five-letter fine dining: Pujol, Xokol, and now Tzuco. I wasn’t expecting to find some of the very best Mexican food I’ve had the pleasure to experience this side of the border in Chicago, but that’s exactly what happened.
When making a reservation, the only option remaining was a seat at the Kitchen Counter; after visiting, I’d say this was the best seat in the house. At the counter, you get a front-row seat to the action: the reduction of the broth for the mejillones, the precision of the application of salsas, and the sizzle and snap of a gloriously made burger (yes, a burger).
Monthly, Chef Carlos Gaytán rotates regional specials in a “Back to My Roots” series, in addition to serving elevated versions of the classic dishes you love. Everything on the menu was tempting, but we landed on two appetizers and a main dish to share.
Even my “I don’t like avocados” fiancé couldn’t resist the most heavenly guacamole, and the chicken tinga tetela had the perfect balance of filling and masa. The cochinita pibil fell to pieces at the mere sight of a fork, so tender and perfect paired with handmade tortillas. The portions were so generous that a third person could have easily joined us, but the team at Tzuco gilded the lily by bringing the most fetching dessert: a corn cake with popcorn and saffron ice cream. The sweetest ending, indeed.
—
Obelix
Obelix | 700 N Sedgwick St, Chicago, IL 60654
I have yet to enjoy a good French meal in Charlotte, so I try to seek one out now and then when I travel. Obelix fit the bill and answered my query about where to have Sunday brunch in Chicago. The menu is relatively small, but the price point range is vast, from a $6 croissant to a $120 caviar sandwich.
Do not be fooled by the dainty-looking slice of quiche above; it was as rich as custard, and I could only finish half (regretfully, I couldn’t package up the rest). The raclette burger, on the other hand, boldly announced its presence as a half-pound patty oozing with cheese and served with a montagne of frites. Reservations essential.
—
Labriola
Labriola | 535 N Michigan Ave, Chicago, IL 60611
I promise I’m only being a little bit dramatic when I say that Labriola saved our trip. Not realizing that there is more than one style of Chicago Deep Dish pizza – some have more of a pie crust base, some are more like a pan pizza (here’s a little more info from food deep-divers Serious Eats) – we first headed to Pizanos to split a pie.
Coming from the first family in deep dish, I had high expectations (and having dined at Lou Malnati’s on my last Chicago visit, I was inclined to give somewhere new a try), but was underwhelmed with the resulting ultra-thin, underbaked crust and skimpy toppings.
Determined to not leave Chicago without a great slice in my belly, we turned to one of the city’s most beloved bakeries, reasoning any baker worth their salt would fashion a pie with a great base. With a location right on Michigan Avenue (also known as the Magnificent Mile), it was a short walk from our hotel – and ordering online meant we didn’t have to spend precious minutes waiting for it to bake.
You see, these beasts of pizza glory can take upwards of thirty or forty minutes to bake properly – time we didn’t have, as we were due at the airport soon after. With just the right ratio of crust-to-cheese punctuated with tangy sauce and hearty sausage, it was exactly the Chicago Deep Dish experience I was looking for. And despite my best efforts, couldn’t finish. Thankfully, there was plenty to share with our new friends at our hotel.
—
Coffee + Bakeries
Sawada Coffee | 112 N Green St, Chicago, IL 60607 Caffe Umbria | 346 N Clark St UNIT 4709, Chicago, IL 60654 Goddess and the Baker | 33 S Wabash Ave, Chicago, IL 60603 Good Ambler | 216 N Peoria St, Chicago, IL 60607 Levain Bakery | 840 W Randolph St, Chicago, IL 60607
If you’re anything like me, coffee is an essential part of taking any short trip. Thankfully, Chicago seems to agree with the necessity of this perky beverage. One unexpected place to find excellent coffee is inside Green Street Smoked Meats, at Sawada Coffee. This shop is owned by world-renowned barista Hiroshi Sawada, making it a must-visit for their amazing coffee and espresso drinks. If you live in Portland, Seattle, or Miami Beach, you may be familiar with Caffe Umbria. This cafe in River North is where you’ll find espresso that might just transport you to Italy. One final solid cup of coffee in Chicago can be found at one of the locations of Goddess and the Baker. For most, the draw will be the sweets (which looked delicious!), but we were already full from the two bakeries below.
Don’t be surprised to see chocolate-covered Oreos at Good Ambler; this bakery is set inside the headquarters of Mondelēz International. But you’re here for the flaky pastries – and maybe a chocolate or two, if you have room. Finally, I hope you don’t dismiss me as pretentious for this next statement, but I feel I need to get it off my chest: Levain Bakery cookies just taste better in New York. But if you’ve never had one before, I think you should still give their Chicago location a visit.
WHERE TO STAY IN CHICAGO
Choosing where to stay in downtown Chicago is an almost overwhelming task; hotels in this part of the city are ripe for the picking. Thankfully, I found the sweetest one:
Staypineapple Chicago, An Iconic Hotel
Staypineapple Chicago, An Iconic Hotel | 1 W Washington St, Chicago, IL 60602
I audibly gasped when I opened the door to the Millennium Park View King Suite at Staypineapple Chicago, An Iconic Hotel.
This was after being already wowed by the hotel’s proximity to the L station, the kind welcomes we received at the check-in desk, and taking in the unique historic touches throughout the lobby restaurant and elevators.
A corner room with windows facing clear North and East meant the first thing in my view wasn’t the spacious living space and work area, the plush king-size bed, or the perfectly lit bathroom – it was the marquee of the Chicago Theatre, twinkling down below. Following the room’s edge around to the opposite corner left me looking out at Lake Michigan, in its signature vibrant blue-green hue.
Only after indulging in the view did I finally turn around, equally wowed by the room I would call home during my stay in Chicago.
We joked that everything is Pineapple at Staypineapple, but… it’s kind of true and in the best way. From pineapple water and pineapple cookies in the lobby to a pineapple paper-wrapped roll of TP, the hotel stays true to the theme in a playful way. Discovering each pineapple element became a bit of a competition for Michael and me – each of us clamoring to be the first to announce a new fruited find. I found these touches quite charming, the nicest departure from a sterile, serious hotel.
And at the same time, it was refreshing that the hotel didn’t just rely on these touches to make our stay in Chicago a great one. The hotel staff genuinely seem to enjoy interacting with guests, treating each one warmly as they arrive and depart for the day. And the bed is actually as comfortable as the website claims, with smooth sheets, multiple pillow options, and that rare kind of mattress that is both soft and supportive.
With only one night in the city, we didn’t have time to experience all of the amenities Staypineapple boasts. We clocked our miles as our workout, so that meant bypassing the fitness center this time. While we didn’t have a chance to dine at Atwood during this short visit, it was perpetually busy with a trendy clientele. Rainy weather saw the loaner bikes staying warm and dry in the lobby (although we did borrow a signature pineapple umbrella to keep ourselves dry). And though Staypineapple seems to love pets just as much as we do, we sadly don’t have a doggy travel buddy in the family (but we still got to hang out with Dash!).
The impeccable location was enough to sway my vote to stay at Staypineapple Chicago, An Iconic Hotel – but all of the extra touches are the reasons why I’ll seek it out again next time I’m staying downtown!
An exclusive discount for wayward readers: save up to 25% on your Staypineapple visit with code WAYWARD (and have an extra cookie for me!)
WITH MORE TIME IN DOWNTOWN CHICAGO
With more time in downtown Chicago, you might consider purchasing the Chicago CityPASS, which offers a helpful discount on many of the city’s major attractions (just make sure you have the proper amount of time to visit, and that they are places you really want to go – otherwise it might be cheaper to purchase admission a la carte!).
More time in the city would also be a great opportunity to check some of Chicago’s hyper-specific museums off your list, like the American Writers Museum, the International Museum of Surgical Science, or the Museum Of Contemporary Art Chicago. It would also be perfect for exploring more of Grant Park (which surrounds the Art Institute to the South and East), weather permitting.
Perhaps the activity I was most disappointed to miss out on this trip was a free tour with a Chicago Greeter. This program pairs you with a volunteer tour guide who provides an insider’s insight and an immersive tour of Chicago’s neighborhoods. Most tours need to be requested in advance and can last two to four hours, but the Instagreeter walk is held regularly, and only soaks up an hour of your valuable travel time.
And okay, I was also bummed to only have so many meals to eat throughout the weekend, which meant making the hard call to pull restaurants from my list: avec Restaurant, Lao Sze Chuan, and Green Street Smoked Meats are all on my list for next time I’m staying downtown.
But the truth is? Next time I visit Chicago, I’m looking forward to getting out and exploring more of the neighborhoods where people live, work, and eat – and of course, I’ll share all about it here!
KNOW BEFORE YOU GO: DOWNTOWN CHICAGO
Chances are, if you’re flying to Chicago, you’ll be flying into either O’Hare (most of the legacy and international carriers) or Midway (Southwest and budget airlines) – but regardless of which route you choose, you can be on the streets of downtown in about an hour thanks to direct service on the L. To spend less time fiddling with ticket machines at the station, you can order a Ventra card in advance, and add transit fare or passes to have ready to go upon arrival (U.S. addresses only, delivery in 7-10 days). My preference is always to select a reloadable card so I can use it on return trips, and in this case, I already had a Ventra card stashed away for use. But don’t fret if you don’t have time to place an order – Ventra cards and paper tickets are both available for purchase from the corresponding machines.
A 1-Day Pass is just $5, which feels like such a bargain (if you’re staying four days or more, you can add a 7-Day Pass for $20). Having a car in Chicago is a major burden, not just because of traffic or navigating one-way streets. Parking downtown is incredibly expensive, and frankly, not worth it. If you’re combining your Chicago trip with a road trip, either return your car early before visiting Chicago or pick it up at the end of your stay in the city to save yourself the money and the headache.
Should we talk about safety? If you’re wondering, “Is Chicago safe?” it might be reassuring to share that we experienced zero situations that made us feel unsafe during this trip (or a prior trip). Many big cities in the U.S. have a reputation for violence, but what often goes overlooked is that most of those instances of violence are targeted or occur within a small geographic area. I mean, Chicago didn’t even crack the Top 15 on this list of most dangerous cities published just prior to this visit. That’s not to say visitors can’t experience crime – you should always use your city smarts – but bad things can really happen anywhere (even at home).
On to a lighter subject – when is the best time to visit Chicago? For most visitors, that answer is going to be “anytime except for deep winter.” Winters in the Midwest are notoriously harsh, but spring, summer, and early fall can be glorious. While I subscribe to the belief that there’s no such thing as bad weather, only bad clothing, there’s value in being comfortable walking around the city. Because of this – and the fact that some of Chicago’s attractions run seasonally – I personally wouldn’t visit any earlier than late March or any later than early November if I could help it.
FINAL THOUGHTS ON SPENDING A WEEKEND IN DOWNTOWN CHICAGO
If you made it this far – kudos to you! This is certainly a long guide for a short weekend.
That in and of itself speaks volumes about just how wonderful a destination Chicago is for even the quickest getaway. With plenty to see and do and a well-connected transit system that can get you there quickly, it’s an ideal choice for weekend travel. If your local airport frequently offers low fares to Chicago, why not aim to see the city one neighborhood, and one weekend, at a time?
I know one thing for sure – it won’t be another eight years before I return to visit again!
A big thank you to Staypineapple for your generous hospitality in hosting our stay, and to Wendella Tours and the Art Institute of Chicago for providing complimentary tickets and allowing us to share your uniquely Chicago cultural attractions.
Enjoyed this post? You may also like:
- Traveling Light: Chicago Packing List
- 33 Hours in Indianapolis, Indiana
- The Best of Brew City: The Ultimate Weekend Travel Guide for Milwaukee, Wisconsin
- Traveling Light: Packing List for Milwaukee, Wisconsin
- The Essential Weekend Travel Guide to Cleveland, Ohio
- How to Spend a Long Weekend in the Twin Cities of Minneapolis-Saint Paul, Minnesota
- Traveling Light: Minneapolis–Saint Paul Packing List
- Weekend Travel Guide: St. Louis, Missouri
- Traveling Light: St. Louis, Missouri Packing List
- Kansas City Guide: Day One, Day Two, Day Three
- Traveling Light: Kansas City Packing List
- Brunch at Milktooth in Indianapolis, Indiana
- 36 Hours in Lower Manhattan
- 10 Tips for Overcoming Museum Fatigue
- 13 Things You Should Know Before You Book a Flight with Avelo Airlines
- Contour Airlines Review
- All Travel Guides by Destination
- Checking In: Hotel Reviews
- Shop My Closet
- Exclusive Promo Codes + Discounts
What are you looking forward to the most during your Chicago visit? And if you’re local, what neighborhoods should I visit next?!
Thanks for sharing! Goddess and the Baker is a great spot.
It really is! What is your favorite thing on the menu?
My whole family of seven including me are going for Labor Day weekend. Thank you for the write up! I was feeling overwhelmed!
Planning a trip to such a large city can be daunting, and I’m happy I could help! I hope you had a wonderful time!
Hi Alyssa! Your Chicago travel guide is so detailed and informative! I love how you highlighted the architecture tour and the Art Institute.
Thank you, Grace! The city has so many incredible cultural sights and opportunities, doesn’t it?
This 36-hour downtown Chicago guide is excellent! Ideal balance of well-known attractions, regional cuisine, and undiscovered treasures. Perfect for a short yet rewarding trip to the city.
Thank you so much, Fathima! A quick trip provides unique travel challenges, but I’m thrilled with how this itinerary turned out (and personally, I can’t wait to return and continue exploring the Windy City!).
I like to see Cloud Gate . This is one of those places/sites that you must see if you are in Chicago. I also like how you can see a reflection of the cityscape when you look at it..
Chicago is a foodie’s paradise. I tried so many delicious restaurants and street food.
Love seeing your suggestions! Labriola’s was an amazing Chicago deep dish experience and definitely worthwhile checking out!