7 Things to Do on A Couples Weekend Getaway to Chicago

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When people ask me about my favorite cities in the US, there are a few that will always make my list. Cities like New Orleans, San Francisco, Savannah – and Chicago.

The Windy City is and has been one of my favorite US cities since I visited for the first time in college.

I love the architecture, the food, the museums, the location on Lake Michigan, and how easy it is to get around in Chicago. It's one of the top places I recommend people visit if they're looking to plan a weekend city break in the US.

Chicago from the water
Chicago architecture

So when Greyhound approached me about traveling somewhere with them from my home base near Cleveland, Ohio, Chicago was one of the first cities that came to mind.

I'd been to Chicago a handful of times already, but my previous trips had been with friends and family members. This time around, I wanted it to be a couple's trip and invited my partner Elliot to come along.

Chicago Theater
Downtown Chicago

Things to do on in Chicago on a long weekend

We arrived in Chicago on a Friday evening and had two full days to enjoy the city, plus some time on Monday morning before catching our bus back to Cleveland.

If you're planning a similar trip to Chicago, here are all the highlights you won't want to miss:

1. Take an architecture tour

Chicago is known for its architecture – it's the home of the skyscraper, after all! – so you'll definitely want to get up close with some of the city's unique builds.

The most famous architecture tour of the city is the boat tour operated by the Chicago Architecture Foundation on the Chicago River. The 90-minute cruises cover decades of Chicago's architectural history, and are one of the best ways to see the city.

Architecture boat tour in Chicago
Architecture boat tour
Architecture boat tour in Chicago
Views from the Chicago River

If you're in the city outside of the CAF's operating season (river cruises only run April-October), though, don't worry; there are still plenty of options.

On our trip together, Elliot and I booked an interior architecture walking tour that took us into some buildings we probably would have never visited otherwise!

Along with seeing the Tiffany dome at the Chicago Cultural Center, we also visited the former Marshall Fields building, traversed some of Chicago's underground Pedway, and even visited a church inside a skyscraper. Chicago's architectural history is so fascinating.

Chicago Cultural Center
Inside the Chicago Cultural Center

(Unfortunately the exact walking tour we took isn't offered any longer, but this one is really similar!)

2. Go to an observation deck

Chicago has two very tall towers, each with a very cool observation deck near the top floor.

The most famous is the Skydeck at the Willis Tower (formerly the Sears Tower), but 360 Chicago at the John Hancock Building is also a great option for city and lake views.

View of Chicago from Willis Tower Skydeck
View of Chicago from Willis Tower Skydeck
Sunset over Chicago from John Hancock Building
Sunset from 360 Chicago

Elliot and I visited both with our Chicago CityPASS (get one of these if you plan to do a lot of sightseeing!), but the experience is fairly similar at both.

If you need help deciding which one to visit, check out this blog post.

On The Ledge at the Skydeck in Chicago
Sitting on The Ledge at the Skydeck
Tilt at 360 Chicago
Tilt at 360 Chicago

RELATED: Willis Tower Skydeck vs. Hancock 360 Chicago: Which Is Best?

3. Get your geek on at a museum

Chicago has some world-class museums, which are great for a rainy (or windy) day. The most famous museums include the Field Museum of Natural History, the Museum of Science and Industry, the Museum of Contemporary Art, and the Art Institute of Chicago.

But don't forget the Adler Planetarium and the Shedd Aquarium, too, both of which are located on “Museum Campus” along with the Field Museum.

Shedd Aquarium
Museum Campus

I love the Museum of Science and Industry (they have a WWII-era submarine and a whole room just about the science of weather!!), but on this trip Elliot and I visited the Field Museum. It was my first time there, and I was blown away by the quality of the exhibits. Two and a half hours was not enough time!

Amanda and Elliot at the Field Museum
Elliot and I with SUE at the Field Museum!

4. Check out some parks

Chicago has a lot of green space and public park land – and a lot of it is close to the lake shore.

If you're looking for a great place for a walk, head to Millennium Park and Grand Park. Here you'll find the famous Cloud Gate sculpture (AKA “The Bean”), the Jay Pritzker Pavilion, Buckingham Fountain, and more.

The Bean
The Bean on a sunny Saturday
Jay Pritzker Pavilion in Chicago
Jay Pritzker Pavilion
Buckingham Fountain in Chicago
Buckingham Fountain in Grant Park

If you have your walking shoes on, you can actually walk all the way from Millennium Park through Grant Park to Museum Campus.

5. Eat deep dish pizza

You can't really visit Chicago without trying some of its famous deep dish pizza. I took Elliot to the original Gino's East on Superior since it was really close to our hotel, but there are tons of options for deep dish in the city.

Deep dish pizza in Chicago
This is definitely knife-and-fork pizza!

Tip: Deep dish pizza usually takes 45-60 minutes to cook, so be sure to allow yourself enough time for a long meal!

RELATED: Pizza, Pizza Everywhere: An Outing With Chicago Pizza Tours

6. Enjoy some cocktails

This was my first trip to Chicago where I made it a point to try some of the best bars in the city – mostly because Elliot enjoys a good Old Fashioned every now and then.

DrumBar (a speakeasy-style bar with a rooftop deck) was right at the top of our hotel, and we also made our way up to the Signature Lounge at the John Hancock Building one night.

Amanda at the Signature Lounge
At the Signature Lounge

The Signature Lounge is located on the 96th floor of the John Hancock Building, meaning you get amazing views out over Chicago along with your drinks.

Go up here after dark to see the city illuminated – you can skip the observation deck line, and get the same view for the price of a beer or cocktail.

Chicago skyline at night
Chicago at night from the Signature Lounge

7. Laugh at some improv comedy

Another of my absolute must-dos in Chicago is to see some improvised comedy. Chicago is home to Second City, an improv school and performance center that boasts alumni like Bill Murray, Steve Carell, and Tina Fey. But Second City isn't the only place to catch live improv in Chicago – there are tons of shows and venues to choose from!

I decided to take Elliot to see my very favorite show in Chicago: the Improvised Shakespeare Company. During each show, the cast totally improvises a complete play in the style of Shakespeare, based on title suggestions from the audience.

Elliot was a bit skeptical, but afterwards even he agreed that this group is phenomenally talented (and very, very funny).

Chicago architecture

Where to stay in Chicago

We stayed at the Raffaello Hotel for this trip, which is located a block from the John Hancock Building and Michigan Avenue and within a 10-minute walk of the Red Line metro.

The hotel has large rooms, an in-house donut shop, and one of the best bars in the city (DrumBar) on its top floor.

Read reviews of the Raffeallo | Book a room at the Raffaello

Or check out these other Chicago hotel options:

  • The LanghamThe top-rated hotel in Chicago, perfect for a luxury trip.
  • LondonHouse ChicagoA beautiful and modern downtown hotel that's part of Hilton's Curio Collection.
  • The Talbott HotelNewly renovated in the historic Gold Coast district.

There are also a lot of Airbnb rentals in Chicago, if an apartment is more your speed:

Getting to Chicago

Chicago is extremely well-connected to just about everywhere in the US. O'Hare is a major airline hub with connections to most major cities (including international ones), and the city is also served by trains and buses.

Elliot and I went to Chicago with Greyhound on this trip. We left Cleveland at 12:30 on a Friday afternoon, and our trip took just about 8 hours total.

It takes slightly longer than if you were to fly from Ohio, but the price difference (one-way tickets from Cleveland to Chicago are usually less than $40) and the fact that you don't have to deal with the TSA made it well worth it in our minds.

Amanda and Elliot on Greyhound
On the Greyhound bus, headed to Chicago

I had planned to utilize Greyhound's free onboard wifi and power outlets to get some work done on the ride to Chicago, but found myself perfectly content to listen to music, doze a bit, and watch the Midwestern scenery outside the bus window instead.

For those who haven't traveled with Greyhound before (or who haven't traveled with them recently), the buses have improved a lot. Now they come with comfortable leather seats with power outlets, free cell-signal-based wifi, and overhead bins large enough for most backpacks and small carry-on bags.

And, even though we weren't on an Express route, the ride didn't really seem all that long.

Traveling with Greyhound reminded me that there ARE alternatives to driving and flying in the US, which is something that I feel like I often forget when traveling in my own country.

While I definitely think road tripping is one of the best ways to see America, the fact is that I would never want to drive to Chicago for a long weekend – the traffic is insane, and parking isn't cheap. Going by bus was a great alternative.

The "El" in Chicago
Plus, once you're there public transport is great!

(You can check out Greyhound's route map here to see where all they go.)

37 Comments on “7 Things to Do on A Couples Weekend Getaway to Chicago

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  1. its great as your other articles : D, thanks for putting up.

    Hi! Thanks for the great post(:
    Other than Gino, do you have other recommendations for deep dish pizza?

      Giordano’s, Pequods, and Lou Malnati’s are also good bets for deep dish/stuffed pizza in Chicago!

    Oh, now this is FUN. My husband has taken Greyhound to meet me when I had to go ahead of him on trips, and he loves the retro feel of it. We’ll have to try a full on Greyhound trip like you have at some point!

      I’m not sure I’d want to do an overnight trip on a bus (mostly because I can’t really sleep sitting up!), but for a trip that can be done in a day, it’s a pretty good deal! We had a really good time.

    Chicago has so much to offer … I drool at the mention of deep dish pizza. That night time view was killer!

      The nighttime view IS killer! One of my favorites!

    So glad you made it out for some cocktails! I haven’t been up to the Signature Lounge yet, so I’ll have to add it to my itinerary for next time. 🙂

      The Signature Lounge is pretty awesome! Yes, the drinks are pricey, but the views really are incredible, especially at night.

    What an awesome trip! We did a road trip to Chicago last fall from MN and we can’t wait to go back- you’ve got some new ideas for us to see too!

      It’s such a fun city – there’s so much to do! Glad to hear that I gave you some ideas for next time.

    This is such a great post Amanda!

    I don’t really know much about Chicago but I’ve only heard good things especially in connection with Art.

    I haven’t been to that part of America before, but I’ve met a few people from Chicago in Berlin of all places. And they all say that Canada is just across the river, which I couldn’t quite believe! Is that true or am I mixing it with another part of America?

      Hmm you must be thinking of somewhere else. Chicago’s not really super close to the Canadian border. (But it’s still very cool!)

        Awww! A shame, and like – Clazz – An Orcadian Abroad – said, in Europe and in the UK, we have no idea why, when we say Chicago, American expats groan!

        Anyhoo, I found out which American city was across the river from Canada.
        It was Detroit!

        The Detroit–Windsor region is an international transborder comprising the American city of Detroit, Michigan and the Canadian city of Windsor, Ontario, with the Detroit River between them! Cool stuff!

    I love your photos as always, Amanda! I need to go to Chicago one day, being in the UK I don’t know why Chicago gets a bad rep? It’s always been quite high up on my list of US cities to visit! (although not as high as San Francisco!)

      In the US, many people (including our new president) like to say that Chicago is a “war zone” and full of murder and rape and other terrible crimes. And sure, there are neighborhoods you’d probably want to avoid in Chicago, but that’s true of any city anywhere in the world!

    I personally hate driving and don’t own a car anyway, so buses are the main way I travel around the US! I’ve done Megabus too and they’re certainly cheaper but it just can’t beat the network of cities you have to choose from with Greyhound. And about Chicago, I’m not one for big cities normally but I would definitely be willing to give it a shot someday, as I’m also down for any place no matter how big it is as long as it’s cool lol

      Chicago definitely qualifies as “cool” as far as I’m concerned! You should definitely check it out.

    You always have such beautiful, colourful photos, Amanda. You´ve really sold Chicago to me – and not just for the pizza! It looks like you guys had a really romantic, fun-filled weekend, and were definitely brave to go up Chicago 360. I´ve really enjoyed visiting several different places around the US and will have to keep Chicago in mind for next time I´m there.

      Thanks so much, Mark! I do enjoy taking photos – and luckily Chicago is quite photogenic!

    I enjoy taking the bus when I travel. I definitely prefer it over flying because I get to see more of the country! I would love to visit Chicago one day, it looks like such a beautiful city!

      Trains and buses are two of my favorite types of transport – so much less stressful than flying, and you get to see the places you’re passing through. I am perfectly happy to listen to music and just ride a bus or train for hours. 🙂

    Also if you go at Christmas time there’s a really cool German Christmas market! Also Hamilton for the foreseeable future.

      Oh yes I forgot about the Christmas market – it’s supposed to be good!

    I would love to do a couple’s weekend in Chicago. Unfortunately my husband is not too convinced on wanting to visit it, maybe I can show him this to try encourage him!

      Hopefully you can change his mind!

    Chicago looks like the perfect place for a weekend getaway!
    Pizza and museums? My kind of place!

      Exactly! Add in the cool architecture, and it’s one of my favorites!

    My sister and I went to Chicago this summer and we both absolutely fell in love. Some of our favorite things were CH Distillery, the Divvy bike system, and the Winter Garden at the Harold Washington Library (and, of course, PIZZA). I’m dying to go back with my husband this year … your post has me totally checking flights to the Windy City!

      I fell in love on my first trip, too. In fact, I seriously considered moving to Chicago a couple years ago!

    The girlfriend has been trying to get me to go see Chicago for months…looks like I might have to actually do it now!

      Yeah! You definitely should!

    Great tips! Anything longer than a weekend, I always suggest heading inland a bit and exploring some of the great neighborhoods of Chicago, like Wicker Park, West Loop, Lincoln Park, etc, etc. But you covered a lot for a short trip!

      Definitely! Chicago has some really cool neighborhoods – but those are definitely better for a longer (or second or third) trip to the city.

    Now I really want to go to Chicago. I hadn’t realised how much there was to do there. And I didn’t know how cheap the Greyhound buses were – that’s something really worth considering if I ever get round to doing a US tour.

      Yes and yes! There aren’t that many truly affordable ways to travel in the US, but buses are certainly an option worth considering. And Chicago is SUCH a cool city – I never get tired of visiting!

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