A Weekend in Chicago

For our next adventure…


Admittedly, we didn’t have much time in Chicago, but it was great to explore another new city this year.  It seems for every place I check off my list, I just keep adding more to my “Have to go back there” list!

We flew into Midway, using the Southwest Companion Pass again, obviously.  Midway is about a 10 mile drive southeast of the city itself.  With O’Hare over 15 miles driving towards the northeast, you’ll have a ways to go from either airport.  Luckily, Chicago’s public transit system connects both airports to the city center, or The Loop (on the Chicago Transit Authority).  We took the Orange Line from Midway all the way in, and promptly found some lunch near our stop.  With sandwiches from the nearby Cafecito in hand, we walked over to Buckingham Fountain and drew up a game plan for the first day.


Old Faithful..

We were staying a bit north of the city, much closer to O’Hare, so we had the whole day to walk around, and then hit the train in the early evening to get up to the hotel.  Taking full advantage of the day downtown, we decided a small walking tour was best, so we strolled along the lakefront up to Maggie Daley Park.  Growing up by the ocean, I have a very finite view of ponds and lakes.  I mean, ponds are small.  Lakes weigh in at a respectable ‘medium.’  Oceans are big.  Simple, right?  I was floored by the expanse of Lake Michigan.  That lake looks like an ocean.  Complete with marinas, folks on the beach (even in October), and waves.


Although there are a few ‘parks’ making up this lake front scene, I’m going to refer to the whole area as the Maggie Daley Park.  This is the one known for that giant silver bean, officially – the Cloud Gate.  We had to check that out!  For a giant shiny object, it sure attracts a lot of visitors.  The place was swarming with tourists, but it was really cool.  Definitely one of my “check off the list” moments.

The next day, while I was at my conference (see below), the other two got to explore the city a bit on their own.  I learned plenty of new things at the Chicago Seminars, but it seems I didn’t have nearly as much fun as they did exploring the city!

Navy Pier

Out on the lakefront, just north of the bean, Navy Pier houses plenty of shops and things to do.  The pier itself has taken many rolls throughout its life, but it’s always been a great place to explore some of the Chicago feel.  The pier is also included on the National Register of Historic Places.

My family explored Navy Pier while I was at the conference, so I didn’t get to check it out myself, but they had great reviews of The Centennial Wheel and the Skate by the Lake rink on the pier.  The Centennial Wheel is a bit pricey ($15 adults, $12 kids) but the views are killer (see featured image above).

Adler Planetarium

Chicago has some fantastic museums in the city, and while we didn’t get a chance to go to all of the institutions I would have liked to, we were able to hit the Adler Planetarium and Field Museum during the weekend.  We picked these two in particular because they seemed interesting, and we were able to take advantage of our local museum’s reciprocity program!  We’ve been members at the Museum of Science in Boston for a few years now, since the price is worth it after only 2 or 3 trips there.  Since the MoS is a member of both the Association of Science and Technology Centers (ASTC), and the Association of Zoos and Aquariums (AZA), they have a fantastic reciprocity program.  The Adler and the Field are both members of the ASTC, so our membership got us into both museums absolutely free!

They visited the Adler after wandering Navy Pier, so I didn’t get to see this one myself either.  According to the report though, the Sky Theatre is awesome, and the whole building is filled with great information.  There are massive pictures and diagrams of objects found in space, along with plenty of activities for kids (and hands on parents) to try out.  I was very jealous of the ‘hovercraft’ the kiddo got to build..

The Field Museum

The Field Museum was amazing.  Plan to spend at least 2-3 hours there if you can.  Double that time if you’re a museum person.  We didn’t have to pay admission, courtesy of the ASTC reciprocity program, but we did check our two larger backpacks for the day (only $3 apiece).  Checking our bags allowed us to explore the museum in leisure, and leave for lunch later without lugging our stuff around the city.


One of the main attractions here is Sue, the T Rex skeleton.  Sue is the largest, most complete, and best preserved Tyrannosaurus fossil in the world, and she was found right here in the states!  Coincidentally, only a few hours from where my family lives in South Dakota.  The fossil is magnificent, although she seems slightly smaller in person than on Jurassic Park.



My favorite section of the museum had to be the Native American exhibits, and specifically the Pacific Northwest art.  Looming overhead in one of the darkest rooms in The Field Museum, the carvings on the totem poles seem to come to life.  As I walked through, fascinated by the details engraved on the wood, my son gripped my hand a bit tighter, worried we might have some kind of a “Night at the Museum” experience.

We explored the Field for a solid 2 hours, and then caught an Uber into the city for a bit of lunch.  Leaving our bags at the museum, we actually went back after lunch for about another hour, meeting up with a friend from Chicago!

Pizano’s Pizza

Ok, ok.  I get it.  Deep dish is tourist pizza.  But you still have to try it, right?!  I actually really like deep dish, tourists be damned!  We had actually planned on heading to a Giordano’s location nearby.  Chatting up our Uber driver, she quickly rerouted us to a place called Pizano’s, a little further away.  I have a feeling everyone has their own pizza place they favor, and she was confident we’d have a great lunch there.  We did!  I’m a huge pizza fan, and I genuinely enjoyed the deep dish there, as well as an Italian sausage roll we ordered.  Luckily for me, Pizano’s ships within the US!  (Although I’ll probably just wait until the next time I’m hanging around Chicago..)

The Chicago Seminars

So, the whole reason I was in Chicago:  The Chicago Seminars.  Hosted by some Flyertalk folks, it’s basically a low-key annual conference on points, miles, and travel hacking.  Having been in the game for about a year, I thought it would be a great way to celebrate!

Now, I can’t post too much on the actual content of the seminar, but I can say it was a great learning experience.  Quite a few bloggers were there, as well as my favorite company to sell gift cards to.  If you’re interested in really learning more about the hobby, look into the Seminars for next year.  Totally worth it.  Maybe I’ll see you there!



I did not realize how much a single weekend in Chicago could cost.  And we didn’t even stay downtown, or do anything high-class.  Here’s the breakdown:  $136 on transportation (not including the flights booked on points), $212 on the hotel for the weekend, $156 on food, $160 on activities, $24 on souvenirs.  Total of $689 for 3 people, 3 days.  $77 per person per day (PPD).

There’s a catch, though.  This was definitely a business trip for me.  The Chicago Seminars had plenty of information on reselling and gift card arbitrage.  Plus, I was able to meet some other bloggers and learn from them while there.  So, after taking out the Seminar cost of $105, and half the hotel cost for $212, I’m at $478 for the weekend, or a PPD cost of $53.  A little nicer, right?  I like to see trips within the $40-$60 PPD range.  If that’s after travel hacking, so be it.

How about without the travel hacking though?  Well…I’ll let you look at the numbers, but it isn’t pretty.  Without travel hacking (but including the business expenses) we have a PPD of $144.  Take out those business costs too and you’re still at $121 PPD.  At that $121 rate, travel hacking saved us just over 56% of the sticker price for this trip.  That’s huge!



I’ve only taken 4 trips since travel hacking.  Disney World, Mexico, DC, and this weekend in Chicago that you happen to be reading about right now.  Disney was tricky – I didn’t really plan the trip myself, it was a bit short notice, and it was my first time hacking.  Including the savings from my Chase Disney card and the Barclay miles I used towards the flights, I only saved around 14%.  In each of the other three adventures, I’ve saved at least 44% of the total upfront cost, by redeeming points or booking with miles!

That’s the reason I’ve fallen for this hobby.  I’m able to travel for cheap.  I don’t feel bad doing it, and I’m not stressing about my bank account balance while I’m exploring.  Plus, no FOMO for me.  I’m still traveling better than most of the people I know!

Chicago was my last trip for a while.  We’ll be hanging out with our local family for the holidays, and don’t have any travel planned until further out, probably sometime in early summer of 2017.  Once Southwest opens up flights for June, you can bet I’ll be on the website, clicking “Add Companion” to every flight I book!

I’m hoping to write a bit more on some of the deals I’ve been using over the holiday season.  There’s tons of opportunities to stack savings and points as we gear up for the holiday shopping season, so I’m looking forward to it!

Comments are closed