Chicago: 48 Hours in the Magnificent Midwest

I first discovered Chicago in 2013, and have been fortunate enough to return several times since, usually for 24 or 48 hours, so I highly recommended this HIIT city destination. 

I also managed to fit in a 12 hour shopping trip layover when I visited Belize in April 2016.

A serial East Coast traveller (remember when everyone travelled to New York for a weekend break?) a work opportunity arose that saw me book a flight to Chicago for onward travel to a little student town called Champaign; four-hour return Amtrak trip, and well worth a visit for a true taste of America (they even have a freakin’ Dairy Queen).

Flights are around 9 hours direct from the UK, and, depending how organised you are, range from £500-£800 for economy return.  

For reasons I’m about to go into, I enjoy staying at Hilton O’Hare (the only airport hotel; handy for layovers) or the Hilton Rosemont (one MTR stop from O’Hare and an entertainment haven).  City-centre hotels are very competitively priced, stay near the Magnificent Mile to hit most of the attractions.

Must-eat Meals
When in Chicago, you have to try the Deep Dish Pizza.  Available all over the city. Garretts’ gourmet Popcorn is a perfect souvenir...just make sure you buy a few bags for yourself.  A great Ghiradelli chocolate shop offers you a free chocolate on arrival, each time you walk through the door; do with that information what you will.  Every other snack and restaurant chain is available.

Okay, okay, so what should I do with 48 hours in Chicago?

This is my favourite destination in Chicago, actually located one stop away from O’Hare airport in Rosemont on the CTA transport system - a well-packed entertainment district. There are massive discounts available in the mall; I love Kipling, DKNY, Coach and Bath and Body Works visits (it was also the only place I visited with my 12 hours).

Note: you might want to make this your last stop before travelling home, and make sure you meet your airline’s luggage requirements.  You can also buy suitcases here if you need to, thanks to staple department stores.  

Chicago is a walking city (there’s a handy Sketchers outlet in the Mall, too) and this is a great shop-sights-walk-rest-repeat must-do.

There are plenty of river cruise options ranging from 40 minutes to an afternoon; we chose a tour that led to Lake Michigan, one of the five Great Lakes of North America - eye-popping views of the city, and at one point you can’t see land, so definitely not your average lake. Detailed historical commentary is provided, too, including the city location buildings that appear in films.  You’ll also find out why Chicago is named the Windy City.  It’s not just to do with the weather.

Ah, a great place to lose track of time.  Get here early to enjoy a full day of strolling-eating-drinking-shopping-repeat before you head up the ferris wheel.  Plenty of souvenir shops, too.  I love eating (and drinking) at Jimmy Buffet’s Margaritaville restaurant, because I love country music, and these places just don’t exist in the UK.

Head to the beach
Yes, really.  Take advantage of this city-by-the-shore and dip your toes in the water (Lake Michigan). Watch out for black biting flies who like a little snack. Take suncreams, bug repellent and suitable clothing as appropriate. The city is literally minutes away though, in case you forget anything. Or need the air-conditioning malls.

Get your sport on
Like sports?  Or live music? You’ll be wanting to head out to Wrigley Field, then, home of the iconic Chicago Cubs baseball team.  Like the other b-ball game? You can catch the Bulls at the United Center, or see the ‘hawks carve the ice in the sport that knocks the socks off of them, to you and me.

Kids in Chicago
I’ve yet to take Mini-S15S to Chicago, but when I do, there are child-friendly places all across the city, including parks, museums, zoos and indoor play areas. Check out this TimeOut guide for details.

Awwww, actually there’s enough entertainment to occupy a week - I’m off to Skyscanner to look at 2017 flights….

Have you been lucky enough to visit Sinatra’s Kind of Town? Or has the Midwestern Marvel ventured onto your travel bucket list?  

All views and costs were my own; I received no sponsorship or funds for this post.  I just wanted to share a fabulous city with you, Dear Reader.


  1. Isn't Chicago great?!? There is so much to see and do there. I have been there at least a dozen times and I find something new every time I go! I didn't realize they had a Jimmy Buffet Margaritaville restaurant. #CityTripping

  2. May is normally the month I'm in Chicago, and very much homesick for Illinois. Didn't even find room to write about the JoAnn's fabric shopping, or the Hobby Lobby dreaming :)

  3. I must say I wasn't overly impressed with the deep dish pizza when I visited Chicago but then again I do prefer thin based pizza. But on the other hand Garrett's Gourmet popcorn!?! I'll have a couple of bags of those please ;)

  4. I know, Garrett's chocolate covered popcorn is gorgeous! Imagine a cruise along Lake Michigan now with a massive bag!

  5. Chicago is high on my list of US cities I'd love to visit - great starting points for me when I finally get there. Thanks for linking up with #citytripping

    1. Glad you found my post useful... Let me know if you'd like to take a Personal Shopper along on your inaugural trip down Chicago way :)

  6. Chicago looks like such a cool place to visit! I want to fill my face with the Deep Dish Pizza...! #CityTripping

    1. Be sure to pop back and let us know how the pizza went on your #citytripping travels :)