Chicago, The Windy City

We visited the Windy City in August 2024 landing into O’Hare airport on a Thursday afternoon. We travelled into the City using the subway - taking the blue line subway towards Forest Park (getting off at Washington) and then changing onto the red line towards Howard (and getting off at Grand). This was the closest subway to our hotel.

Our hotel, the Hyatt Centric Magnificent Mile was located around a 6-7 minute walk from the subway. A nice hotel with a Starbucks on the ground level, you enter through revolving doors into a lobby, it is a little confusing as although there is a desk, it is not constantly manned and we didn’t realize that we had to take the elevator up to the main lobby area to check in.

This hotel did charge a resort fee of $20 per night and we stayed on a room only basis. Breakfast was available to purchase at a cost of around $35 per head and the buffet on offer was plentiful and was served in the restaurant area on the lobby floor. When checking in we did get a $35 voucher which covered the price of one breakfast.

From the hotel lobby we took the elevator up to our room. Rooms consist of two double beds with a TV, desk and chair etc. The room had a decent sized closet and a pretty standard bathroom, however as we were on a trip visiting 7 cities in 18 days we rarely unpacked!

We turned left outside the hotel and then left again down E Erie Avenue to the Magnificent Mile and then wandered along the shops for a while, stumbling across a five storey Starbucks! Roasters! This place is worth the visit not just for the coffee but there is a huge amount of merchandise on offer and there is a novel curved escalator to take you up plus a roof top area.

We then headed across to Lou Malnatti’s for deep dish pizza - the restaurant we chose was the River North branch and we booked in advance via their website. Our pizza was just as described, deep! We’d chosen bruschetta to start which came quickly and consisted of about 8 pieces of tomato and basil topped bread so we were half way full before our pizza even arrived! The pizza was delicious but we did ask for a take out box. Despite this we had to sample a dessert (shared of course) and opted for tiramisu which was delicious. We headed back to our hotel afterwards, on foot, which felt perfectly safe despite being quite late in the evening. There was a local Seven11 near our hotel which did attract a fair amount of people and there were a few homeless guys around, but no-one bothered us.

The next morning we used our voucher to get one free breakfast and paid for another at a cost of $21 for the continental option. We then headed off on our crazy Chicago day!

Heading out first to the Ogilvie Transportation Centre (OTC) to pick up our train to Winnetka to find the Home Alone House. We used the Union Pacific North line and our journey took around 40 minutes. You will need to take the train heading for Kenosha. It’s worth noting that if you do turn up early for your train, there is a lovely market in the station where you can buy coffee, cakes, chocolates, fruits and vegetables and much more. I could have easily spent an hour just wandering here!

Winnetka itself is a small town, really lovely, clean and tidy and friendly. We purchased a coffee at the Greenbay Cafe which is located on the corner, and then headed down Lincoln Avenue towards the small crowd that had formed outside the Home Alone House. It is much smaller than it appears in the movies but again, in my opinion as a Home Alone fan, well worth seeing ‘in the flesh’ so to speak. Although visitors are welcome and photographs and videos acceptable, there are signs asking you not to touch the gates etc - at the end of the day this is someone’s home.

From here we headed back into the City and went to find Raising Canes for lunch - chicken tenders, fries, sauce and bread in a basket - cost around $20 but we shared and just got a couple of cokes to go with it. Nice food, nice sauce but what a busy little place that is! Just along from Raising Canes is the infamous Chicago Bean - and what a sight that is! Set on a park that runs across the waterfront area, the Bean is huge, there are other amusements, rides, shops and restaurants close by and its also worth noting that although it is free to enter, there is a security checkpoint that you need to pass through before entering the park.

From here I was quick marched up Magnificent Mile to the Chicago 360. Housed in the John Hancock building, we had paid to visit the top, 94 floors up! Again this was booked via their website and we opted for an inclusive ticket which gave us entry and a cocktail plus a free glass to bring home. We paid an extra $10 each on the day to experience ‘the Tilt’ which was ok, but really not worth the money. There are of course the usual photo opportunities where you are snapped in front of a green screen and you collect and pay for your photos after your visit. We purchased a magnet of the Bean which now resides on our fridge, and one picture of us with the City view behind us.

After this we headed back along Magnificent Mile in search of Crumbl Cookies - a box of cookies later and around $16 we headed to the waterfront area to pick up our Viator architecture boat tour. This is an hour long boat trip along the Chicago River with commentary explaining the different buildings and architecture. We unintentionally ended up on the boat at sunset which to be honest was absolutely beautiful.

We then headed over to Carsons Ribs for ….. well ribs! And very nice they were - a more upmarket style restaurant than I expected, it was actually very reasonably priced and we were topped up with water regularly, well attended to and left well fed!

The next morning we checked out early to catch our next flight to Vegas, having a quick breakfast at the airport. Using the subway, our journey back only took around 40 minutes.

So Chicago - what a really nice place. I thoroughly enjoyed our whistle stop tour; we certainly did quite a lot! If we went back again I would definitely check out the beach area which you can see from the top of the 360 - amazing that there is a beach - you really do forget that Chicago is set on a huge Lake and what you are seeing is not the sea! It is a clean and totally walkable city with some good shopping and plenty of places to eat.

Anyway, off we go to our next stop, Fabulous Las Vegas !

See you soon

Tracey and Georgia x

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