Ok I know I just went to LA for Canada day long weekend, who am I to pack up and head to Chicago for August long weekend. Well I did and we actually planned this trip well in advance. Why you ask? It was a multiple couple trip turned into a friend trip, and everyone’s work schedules are too different to do something last minute. So we rented a Car and booked our hotel and the 10 of us were off! Rented a car all the way from Toronto to Chicago you may ask. Yes, and the ride was 8 hours and one of the best road trips I have been on. Blasting music and singing “we saved $300 each by driving and NOT flying.”
How I saved moola for the important stuff…shopping!
We wanted a fun hotel in a location that was walking distance to everything. We called the W hotel (since they are known to be hip hotels) and found out that if you book using an Amex Credit Card you get the “book 2 nights get the 3rd free” promotion. We got the W hotel City Center for $460CAD for 3 nights. For the car rental one of the 10 people going on the trip had a corporate rate with Budget, and we were able to get a van that fit 6 of us for $550 including insurance.
As it was a long weekend we left Thursday night and only needed to use one vacation day, since the Monday was off!
- I love love love Chi Town! It is literally the best of both NYC and Toronto. It has the lakefront I think Toronto will never have, and it has the great culture and shopping that a big city like NYC holds strong.
- I will call out the W hotel City Center because it was amazing! They have this “whatever wherever” service that basically makes hotel guests' wishes come true. I went to Sprinkles cupcake store and there was a HUGE line up that I did not want to waste my trip waiting for. Sprinkle cupcakes are to die for, I love the coconut, red velvet and black and white cupcakes the best (I experienced these on my LA trip)! So when I realized I would not be getting any I went back to the hotel only to see the whatever/whenever service booth. I thought there is no way they will wait in line and get me those cupcakes but I should try anyway. Turns out they got me my cupcakes and delivered them to my room at no extra charge. I was quite impressed and W hotels definitely do make wishes come true!
- My highlights: Doing a bike tour across the city, dining at Sushi Samba (Japanese/Brazilian fusion restaurant), dancing the night away at Underground and Crescendo. The best part about Chicago in the summer is the great street festivals. We happened to be in one when we went to TANGO SUR. Tango Sur is a Bring Your Own Alcohol restaurant, where literally you can bring bottles of vodka, wine, beer to enjoy with your meal (which happens to be straight from an Argentine grill). BYOB restaurants are quite popular in Chicago and the best part is there is NO CORKAGE FEE! Another great part about Chicago is the beautiful Magnificent Mile which is a less dramatic and scary version of Rodeo Drive. People are actually in the stores on Magnificent Mile (when I was in LA the stores on Rodeo were intimidating as there would be 10 salespeople and 1 person in the store).
- Also, like all big cities like NYC, MIAMI, and LA you can make reservations at top restaurants using opentable.com
- Make sure to check out: Millennium Park, Lincoln Park, Navy Pier, Magnificent Mile, Deep Dish Pizza Store(although I did not enjoy), a Blues clubs, a BYOB restaurant, and the artificial sand beach on the lakefront!
- I absolutely fell in love in Chicago and had the time of my life! Looking forward to my next trip back.
Kicking off the bike tour
A Chicago Street festival near Tango Sur
Lou Mitchells the BEST BREAKFAST place
The famous BEAN
I do not understand the fuss about DEEP DISH, it was not good.