Friends are always asking me for tips on Chicago. I have never lived there, mind you, but I’ve been there an awful lot. You see, it is by far this solo traveler’s favorite US city, besides New York, of course. My love affair with this city started with my travel inspiration, my Mom, a true wanderlust woman if there ever was one. Mom and I would pick up and go to the Bahamas for lunch or Chicago for brunch and then home again. The wanderlust spirit is in my DNA and Chicago must’ve been home in another life.
The Windy City is – for want of a better analogy – a clean New York. It offers so much and I cannot possibly squeeze it all here into one article, so look for several more to come. Today we’ll deal with the basics.
How to get there, where to stay, dine and shop – that should be enough to get most single women travelers going, right! I am also, placing this post in the Frugal Friday section because flying to Chicago is pretty affordable almost any weekend from almost anywhere in the U.S. (i.e. – r/t weekend fare from NY is about $170).
First of all, no matter where you are flying from……..avoid flying into O’Hare Airport at all costs. It is the black hole of aviation, the Bermuda Triangle of flight across the U.S. I kid you not. Many travelers have entered into the O’Hare zone and are still in limbo or they have disappeared altogether. Since it is the central hub, smack dab in the middle of the country, O’Hare gets a lot of traffic and passengers suffer delays because of it. Try Midway Airport if you can. It’s a smaller airport and close enough to the city to be convenient.
Where to stay – If you are flying solo for your first visit to Chicago, you might as well stay along Michigan Avenue, the Magnificent Mile. It is a safe area, even at night, and it contains some of the best shopping you will ever experience. Now, there are many five-star hotels along and around this strip and you can pay the high rack rate or you can do the smart thing and Name Your Own Price & Save up to 50% OFF at Priceline. I have used Priceline on my last three trips to Chicago and have not been disappointed once. You will likely get a very nice room for under $150 and in a major city today, that’s a travel deal, if not a steal.
Where to shop – Certainly everyone will steer you to Water Tower Place. Now that is certainly a convenient place to start your shopping odyssey but by no means should it be your last. There are several other malls and shops all along Michigan Avenue and you can shop till you drop – literally. I’ve been there and done that! As to the souvenirs available – there are plenty and most of them carry the same thing so shop around for the best price. I haven’t listed specific stores here because if you can name it, then Chicago is likely to have it – from Target to Neiman’s, all on the same block. Can you just see that happening on New York’s Fifth Avenue? I was shocked when they let in H & M across from Saks!
Where to dine – Chicago wants to hang its claim to fame on its pizza. Hey, I’m from New York and there are 2 things we do and do well – Yankees and Pizza. Now, I have had some good pizza in Chicago but I cannot tell you that it’s any better than New York………..or Italy! By the way, the last time I was in town I bypassed Uno’s and —- and headed straight for California Pizza Kitchen – there is one in the Water Tower mall and another just off Michigan Avenue on Ohio Street.
Brunch at the Signature Room on the 95th floor of the John Hancock Tower is a must and a definite Sunday splurge. It is set up as a buffet and there is plenty of food, so some of the dishes are hit and some are miss, but when you go to the Signature Room you are not there for the food so much as the views. You have 360 degree views of the entire city and lakefront. It is breathtaking and worth every bite.
Dinner in Greek Town is also a lot of fun. It’s an entire area dedicated to all things Greek and yes, at a place called “It’s Greek to Me” you may still hear sounds of oopah and broken plates as you dine.
OK, I am at over 700 words already and have not even scratched the proverbial surface of my kinda town……so watch this space for more in the near future.