Whirlwind Weekend in the Windy City with TripleSpot & HOW YOU CAN WIN $2000!

by Melissa on October 31, 2013 · 7 comments

Want to win $2000?




TripleSpot – the app that I partnered with to go on my very own weekend adventure to Chicago last weekend- is giving away $2000 to 5 lucky winners who will get to be the next generation of TripleSpotters. For those of you who don’t care about my weekend in Chicago – click HERE to go directly to the TripleSpot contest website. I’ll include more information at the bottom of this post for those of you who wish to stick around.

My Chicago Weekend Adventure

My TripleSpot Weekend Adventure started early Friday morning, the boy and I set off on the road to Chicago – a journey that should have taken us 6hours (if we drove straight without stops).  After just an hour drive from London, Ontario, we arrived at the border at the Blue Water Bridge between Sarnia, Ontario and Port Huron, Michigan. TripleSpot We continued on along Interstate 69 and Interstate 90 for a few more hours until we made a shameful stop at Arby’s for lunch (a guilty pleasure that is difficult to find north of the border in Canada).  Since we were already playing the eating game, I made the boy pull off the highway after I saw no less than 8 billboards for a place called The Chocolate Garden.  Chocolate!  I’m a girl – of course we had to stop.  We walked into the quaint chocolate shop and were immediately overcome by the delicious smell of chocolate.  Not really knowing what we got ourselves into, we decided to try out the ‘tasting bar’ where each of us got to sample 3 truffles.  Needless to say – they were every bit as good as they look and I ended up spending nearly $15 on chocolate truffles for the road! TripleSpot Just a few hundred meters down the road, we saw a cider mill – and of course had to check it out.  I’m a huge fan of apple cider, and it wasn’t the nicest of autumn days.  While I chugged back the taste-bud tantalizing cider, I snapped a few TripleSpot pics of the mill– all on display for the cider mill’s guests to see.

After getting ourselves drunk on apple cider (okay… it was me… not the boy) it was back in the car for us, and we decided to not stop until we hit Indiana Dunes National State Park.  We made a quick pit stop at the visitor’s center right off the highway and got some information.  And since I was feeling cheap – we decided to forego the actual state park, which requires visitors to pay park fees, and opted to park in a lot right next to the State Park, and check out the beach, and walk along the beach to see what the State Park had to offer.  Sneaky sneaky.  We were amazed with the views of Chicago across Lake Michigan, and not so impressed with the many steel mills that littered the beach to the south of the park – towards Gary, Indiana.  Regardless, give me sun, sand and water nearby and I’m as happy as can be. TripleSpot  After checking the time, we realized that we’d been on the road for most of the day, and it was approaching rush hour time.  Chicago was only an hour or so away, so we decided to make tracks and hopefully avoid any traffic.  FAIL!  We hit it.  And sat in stop-and-go traffic for over an hour.  Luckily we eventually made it to our hotel – the W Chicago City Center-  when we did as we were running scarily low on gas.  We gave the car over to the valet, and checked into our “Wonderful Room” and promptly took a lay down after spending 9 hours in the car.

Determined to have a good evening and find a good place to eat that was also close by – I took to some of the suggestions I received on The Mellyboo Project’s facebook page – and we decided upon The Gage, which happened to be only a short 15minute walk from our hotel.  The Gage is out of this world.  We showed up without a reservation on a very busy Friday night, and they were happy to accommodate us.  We settled in, ordered a bottle of the Corte Sant’Alda Valpolicella from Italy and settled upon our appetizers – I chose the golden beet salad with goat cheese and Fuji apples and the boy had scallops with kimchi and chorizo – both incredibly satisfying.  They didn’t last long as we devoured them!  Next, our main’s – the manly meal of house crafted sausages (which apparently are different each time you go), and the delicate, but equally satisfying pan-fried Halibut with Orzo and chorizo. TripleSpot Just when we couldn’t think we could fit any more food in us – the lovely waitress handed us the dessert menu.  And who can say no to sweet potato crème brulee? I can’t.  This was about the time we started talking with the manager – I explained that we were in Chicago as part of the TripleSpot Weekend Adventure, he was excited to invite us over to the bar to sample some of the local craft beers they had on tap.  This was right up the boy’s alley – and if I may say so myself, much deserved after he drove the entire way to Chicago.

All good things, of course, must come to an end, and since we had an ambitious day of sight seeing ahead of us, we decided to pack it in and walk back to the hotel.  Along the way we passed by the iconic Chicago Theatre- with the sign all lit up.  To be quite honest, I was a bit drunk after an entire bottle of wine and a few glasses of local craft beer – so I may have been exceptionally excited to see the sign!  Eventually, the giddiness wore off and we made it back to the W and packed it in for the night – falling soundly asleep on our amazingly comfortable feathertop bed. TripleSpot  We took on the next day at ‘full-steam’.  After a short stop at the post office to send a friend of mine a package, we made our way through the city and over towards Navy Pier.  Admittedly, I didn’t really know exactly what Navy Pier was all about, but once I got there I totally understood the appeal.  Some features include a mini amusement park area complete with a Ferris Wheel, and rides for children (and children at heart), tons of restaurants, a Children’s museum, even a beer garden (which sadly wasn’t open on that brisk autumn day.)  It’s also the place in the city where you can hop on a river cruise or tall ship, and see the city from the water. TripleSpot The boy and I decided to go for the Architectural River Cruise, as so many people suggested we check it out – even calling it a “must do” item.  Since we had purchased the Go Chicago Card (which allowed us entry to 25 different attractions), we opted for the Shoreline Architectural River Cruise since it was included.  Our guide Heather was extremely informative and told us all about all of the major buildings along the riverside including the Trump Tower, Willis Tower (former Sears Tower), Hard Rock Hotel, and so many more.  The hour-long boatride had us cruising along the Chicago River, admiring the architecture and learning all about the history of the city. TripleSpot We managed to work up quite the appetite, so once we disembarked the river cruise, we made a beeline for Lou Malnati’s Pizzaria – another suggestion from my readers- for the world famous Chicago deep dish pizza.  It was 2pm and we were expecting to have missed the lunch rush.  How wrong we were.  We ended up waiting nearly 45min for a table, had rude service from the bartender, but thankfully since we’d ordered while we were waiting, our pizza came shortly after we sat down (at what I like to think was the best seat in the house – right in the front window).  Everything you’ve heard about Chicago deep dish pizza is true.  This pizza was to-die-for!  But we admittedly ate way too much and I’m not sure I can look a pizza in the eye for the rest of 2013. TripleSpot We finished off our afternoon by jumping on the Gray Line Hop-On Hop-Off trolley tour, which pointed out some of the best that Chicago has to offer.  Our guide Antoine, a college student, was hilarious and informative.  He pointed out some important landmarks and attractions such as the Blackstone Hotel (where 12 US Presidents have stayed during trips to the Windy City), Soldier Field (home of the Chicago Bears), The Field Museum, Shedd Aquarium, Alder Planetarium, The Art Institute, even the fountain from the intro to Married with Children! TripleSpot That night, we decided to skip dinner – since we were still uncomfortably full from our massive lunch.  We did decide to check out Roy’s – a Hawaiian fusion restaurant in the “Near North” area of Chicago.  Since we walked in around 10pm we were told the kitchen was closed – I would have liked to try the poke appetizer (regardless of still being full), but we opted to enjoy a few glasses of wine instead. We made it a fairly early night, since our day was so jam packed.  It was also Halloween weekend and all the freaks were out looking to get drunk in their skanky costumes- something I’ve grown a little bit out of in my old age.  Plus we didn’t have costumes.

The next morning, we had only one plan – and that was to go see the famous Bean sculpture in Millennium Park.  And we did!  It was a bit busier than I expected it would be at 9am on the Sunday of Halloween weekend, but we did manage to get some good snapshots.
TripleSpot Since we had a prior commitment in Toronto for that evening, we decided to check out of the hotel and leave since we knew we had at least an 8hour drive ahead of us.  I had such an incredible time in Chicago, despite not getting to see or do as much as I’d hoped (perhaps I got a little too ambitious).  We’ve decided, however, that we will definitely be making another trip to the Windy City – preferably in the summer, so we can really enjoy being out by the water and not freezing our butts off!

For more pictures of the spots I went to during my trip to Chicago– download the TripleSpot app on iPhone or Android and follow me- Mellyboo!

How to Win $2000 with TripleSpot for a Weekend Adventure

Want to go on your very own $2000 Weekend Adventure with TripleSpot?  As I mentioned in my announcement post about my partnership with TripleSpot, it is a great new app that helps users promote amazing places, and helps travellers check out cool spots on their trips!  To try your luck at becoming one of the next 5 Weekend Adventurers and nabbing your own $2000 just follow the easy steps below. triplespot Need inspiration?  Check out the other 4 official TripleSpotters

Candice Does the World – Weekend in Reykjavik 
Backpack With Brock – Weekend in NYC
The Local Traveler – Roadtrip to Montreal and Quebec
Cashmere and Camo – Roadtrip through the Rockies.

While my trip to Chicago was made possible thanks to TripleSpot, I found myself really enjoying the app.  I was excited to share spots with other users.  As a travel blogger I find it’s always great to be able to give tips to other travellers, and TripleSpot makes it even easier!

[EDIT: Nov. 26, 2013] I’M GIVING AWAY $100!

If you’ve already entered into the Weekend Adventure contest to win $2000 – be sure to promote your list using the #TMP100 hashtag and a lucky reader of THE MELLYBOO PROJECT will be winning $100!


{ 7 comments… read them below or add one }

The local traveler October 31, 2013 at 5:42 pm

There is so much great food in this post. I’ve never been to Chicago but this is a sweet itinerary!!


Melissa November 4, 2013 at 1:10 pm

I can’t wait to go back – especially in the summertime! We have so many places we still want to check out. Next time I think we’ll take the Amtrak from Port Huron, MI though- would be way faster and cheaper than driving, and waaaaaay cheaper than flying.


Anne October 31, 2013 at 5:47 pm

Sounds like an amazing weekend. Certainly a place I would like to visit. You outlined it remarkably.


Melissa November 4, 2013 at 1:10 pm

It’s just too bad that we didn’t have longer. Ahhh well… we’ll just have to go back.


Megan November 1, 2013 at 12:58 pm

Seems like a nice weekend. I never really thought much on visiting Chicago except to see friends that live there. But clearly it could make for a good trip. :)
I’m intrigued by this app too. Sounds similar to the idea I had for my thesis project in university that I decided not to make. haha. I may have to test it out.
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Melissa November 4, 2013 at 4:27 pm

It’s a really cool city – and really not far from us, so definitely worth the trip. And if you have friends who live there – all the more reason to go for a visit!

And it’s really cool that you had a similar idea for your thesis project! TripleSpot is awesome -and why not try to win the $2000 while you give it a test run! :)


Kenny F November 30, 2013 at 4:35 pm

Thanks for the chance! I had a blast making my list. Tweet – https://twitter.com/bittripfan/status/406898662011187200


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