See All the Main Attractions of Chicago for Only $35 Per Person

That’s $35.00 per person for three days!!

Not bad, eh?

Okay. So about our trip to Chicago… correction, our SECOND trip to Chicago.

We took our first trip with our boys. Which was fun, but we really didn’t get to do anything WE wanted to do. We spent our time touring museums, which was fun, but I know Kevin was disappointed because we didn’t have time to actually tour the city.

So we went back. Just me and Kevin. And did I mention this was our first trip, just the two of us, in twelve years?? Every other time, we’ve taken the boys. Which was fun, don’t get me wrong, but getting to hang out with just my husband and best friend in the world?

Awesome sauce.

We flew out of Branson. We had planned on using some of our frequent flyer miles (we have so many now that Kevin and I can take THREE round-trip, er, trips now), but honestly? It was actually cheaper to fly out of Branson than it would have been to cash in our miles. And besides, we wanted to cash those miles in on longer flights, like to either coast, than to a city only a little over an hour away.

Branson airport is tiny. As in DINKY. And it looks like a lodge. In fact, it’s so small, that it has one runway – for both take offs and landings. And it was a heck of a lot better than having to drive all the way to St. Louis, which is four hours away, as opposed to Branson, which is only 45 minutes away.

We flew Air Tran and, meh, there wasn’t anything exceptional about it, but then again, I wouldn’t really want there to be. It’s cheap for a reason – don’t expect the royal treatment, but we got up there and back safely, so that’s all that matters.

I actually wanted to stay up there a bit longer than we did (it worked out to be 2 1/2 days), but Kevin didn’t feel comfortable leaving the boys alone for longer than that and it actually worked out better this way anyway – Chicago is great, but we were ready to come home after two days.

We stayed at the same hotel – the River Hotel on Wacker street. (I know – what a name!!). It was $179.00 per night (we booked it through, and though that sounds expensive, actually, that IS expensive, it was worth it to us because the hotel is right across the street from the Chicago River in the heart of downtown Chicago so it was close to everything.


The room itself is small, but we actually upgraded to a room with a kitchenette when we got there, so we saved ourselves breakfast money by just eating cereal every morning.

The hotel has a filtered water station (FREE) near the elevators on each floor, so we also saved ourselves money on bottled water while we were there, too.

We flew into Midway Airport in Chicago. Which is actually a little ways from downtown. I was a little worried about how much money we’d have to spend in taxis while we were there, but I needn’t have worried – when we landed, I noticed that we could take the train directly from the airport all the way to downtown (the orange line). It cost us $2.25 per person to take the train, thereby saving us probably close to $30 or $40 dollars (including tip) if we had taken a taxi from the airport to our hotel. True. We had to lug our suitcase around, but we only took our one big suitcase, since it was only Kevin and me, so it really wasn’t that big of a deal. In fact, Chicago’s public transit system is pretty efficient and we didn’t take one taxi the entire time we were there.


We arrived at our hotel around noonish on June 6th. We checked in, then set about collecting brochures from the lobby and walking around the area to familiarize ourselves with the layout. Kevin noticed quite a few trolleys parked across the street from our hotel and a kiosk with people surrounding it. It was the Chicago Trolley and Double Decker Company. For $35.00 per person, you could ride the trolleys and Double Decker buses around Chicago for three days.

Chicago 2012

They stopped at 14 popular attractions around the city and you could get off, and get on, as many times as you wanted within that three days time. They even had a few night tours so you could see the city lights. Since we wanted to see many of the places the trolleys/buses stopped at, we thought it would be the perfect mode of transportation for us – and it was. We. Had. A. Blast!!! I HIGHLY recommend taking the Trolley/Double Decker Bus tour if you’re in Chicago.

Chicago 2012

You get to see so much within a small amount of time and you really DO get your money’s worth. In addition to the rides around town, you get a free t-shirt, free popcorn at a famous theater and free candy at one of their best-known candy shops. It was like a scavenger hunt.

The weather was perfect the entire time we were there. (Unlike last time, when it rained on us the entire time). In fact, we rode the Double Decker bus late afternoon on June 6th, just to get an idea of the route, and I got downright cold. (Which is saying a lot, considering I’m NEVER cold).

The next day, we hopped on and got off at Navy Pier.


We were both a bit disappointed with Navy Pier. You hear so much about it and indeed, it’s touted as the most popular tourist attraction in Chicago, but I guess I was expecting a little more … SOMETHING. Nearly all of the buildings were empty and the picture above? Is pretty much it. I think one reason it’s so popular is because of the Children’s Museum, otherwise? There simply wasn’t that much there. Still. I’m glad we went and the view of the Chicago skyline was certainly worth the trip.

Chicago 2012

We hopped back onto the trolley and hopped off at Millennium Park. It was packed and I loved it.

We saw the coolest fountains:

Chicago 2012

Chicago 2012

Sculptures …

Chicago 2012

And little parks within the park …

Chicago 2012

An outdoor amphitheater …

Chicago 2012

And of course … the Bean.

Chicago 2012

Chicago 2012

That pretty much pooped us out the first day we were there, but we were ready to go on the second day. We got up and around early on Friday, our last day there, and took an architectural boat ride down the Chicago River.

Chicago 2012

We wanted to take this tour because it would give us a different perspective and it was really interesting to hear the stories behind all of the fascinating buildings in Chicago – it was well worth the money.

Chicago 2012

Afterward, Kevin finally got to eat a Chicago-style hotdog …

Chicago 2012

… (did you know that if you put ketchup on a Chicago-style hotdog, it’s considered an insult to Chicagoians?)

I actually ate at Wal-Greens for lunch because of my funky diet and really, all I wanted was some fruit.


Then we hopped back onto the bus and got off at the Sky Deck at the Sears Willis building.


We were 103 floors up and we got to step out onto a glass box that extended outside of the building.


It was weird and exhilarating at the same time. It felt like you were literally walking out into nothing. But the view was spectacular …

Chicago 2012

… and it was worth the money. (We got a two dollar discount by buying tickets through the Chicago Trolley/Double Decker bus people. Yet ANOTHER reason to take this tour if you’re ever in Chicago).

After the Sears Willis building, we started walking.

And walking.

And walking.

We were trying to find these stupid things …


They’re called “Headless Torsos” and though they were sort of cool to walk among, I’m not really sure they were worth walking two miles and sweating off lunch for.

Chicago 2012

I knew the Buckingham Fountain was close and we HAD to find it. Remember the impressive fountain at the beginning of the “Married with Children” series? Well. We found it.

Chicago 2012

And it was even more impressive in real life. (It actually shoots water straight up into the air like that on the hour, every daylight hour).

By the time we found the fountain and took some pictures, we were both pretty tired. So we sat down and dangled our feet off the edge of a pier to relax and breathe in some Lake Michigan air.


It was so peaceful.

Chicago 2012

We topped off the day by taking one last ride on the Double Decker bus to see Chicago at night.


Our flight left at noon on Saturday, so we had plenty of time to check out and ride the train back to Midway airport. The train was practically deserted on Saturday and it was a relaxing trip back. We got back into Branson about 2:00 and we were back home by 3:00 in the afternoon.

The house was still standing and the boys didn’t look too malnourished, so I’d say this trip away from them was successful. 🙂

Chicago was fun, and we really enjoyed ourselves, but I’m not sure if we’ll ever go back. There are still a few things we would have liked to have seen (the Planetarium and the Natural History Museum), but it’s not something we can’t live without.

Next? We are planning on taking a short, three-day cruise down the Pacific coast in October … of this year. Oh yes we are.

And next summer? We’re thinking about renting a cabin in the Rockies and hiking some trails. And maybe taking a quick trip to Las Vegas next year, too. We’ll see.

Life’s too short to stay in one place for long, don’t you think?

Chicago 2012Chicago 2012Chicago 2012Chicago 2012Chicago 2012Chicago 2012
Chicago 2012Chicago 2012Chicago 2012Chicago 2012Chicago 2012Chicago 2012
Chicago 2012Chicago 2012Chicago 2012Chicago 2012Chicago 2012Chicago 2012
Chicago 2012Chicago 2012Chicago 2012Chicago 2012Chicago 2012Chicago 2012
Chicago – June 2012, a set on Flickr.