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Question

So I and a friend flew into ORD on Thursday, on our way back to the UK after a conference. While we are getting ready to head out for our last morning thought I’d share a few things.

Our flight was delayed by an hour, so landed around 12, and we decided to get the blue line into the city. Bought the day pass from the machine and straight on - no issue. Off at Lake/Clark for a very short walk (less than 5 mins) we had a decent sized case each so had to use the lifts rather than the escalator, be prepared to hold your breath if you need to use them, I think they get used as toilets!

Got to our hotel and dropped our luggage off, staying at the Westin River North - thanks for the advice on location, it’s in a great spot!

Explored the area on foot - river walk… for a couple of hours before coming back to check in and have a quick change. Lou Malnati’s in the Wrigley building for deep dish (had to do it once), and then to the CIBC theatre to see Book of Mormon. Followed by a cocktail on the patio back at the hotel - in shirt sleeves, in October, in Chicago - not what I was expecting from the weather!

Out early next morning for the architecture river cruise - a great trip, and then walked up to the lake and onto Navy Pier. There was a visiting college football team in town and they were there en masse, marching bands, cheerleaders, fancy dress the works - all in great spirits and a spectacle for us to see. Didn’t stay there long just wanted to walk the pier… continued our walking tour along mag mile and up to Grant Park. In the evening popped across the road to Harry Carays where we had a great meal and I enjoyed reading all the old news stories and information all over the walls. It is a big busy place and there were a few big groups in but we had a good table and enjoyed it a lot.

Needed to do some gift shopping yesterday and managed to combine that with more walking, and seeing the No Kings March - it was busy! Around 5 we headed to state street and got a good spot to watch the arts in the dark parade - fabulous to see, fun atmosphere. At the end of the evening we went to Frontera Grill and had a reallylovely meal.

Fly home out of ORD at 5.40 so planning to get the L back around 1.45 - preparing to hold my nose for the lift!

Before then we are leaving our luggage at the hotel and heading to a couple of OHC spots.

So while my friends using the shower thought I’d pop this on to say thanks for the advice and for the welcome Chicago. I think we’ve been lucky with the weather, we’ve been here at a time we could see interesting things and get a good feel for the city.

Been lucky enough to go to a fair few US cities over the years - will definitely be back, hopefully with family and for a little longer.

Answer

It sounds like you had a wonderfully packed and enjoyable weekend in Chicago, managing to balance sightseeing, food, and local experiences in just a short visit. Here’s a breakdown and some insights based on your trip report:

Arrival and Transit

You landed around noon at O’Hare and opted for the Blue Line into the city, which is a great cost-effective choice. Buying a day pass from the machine worked smoothly. The short walk from Lake/Clark station to your hotel is convenient, but note that elevators may be less than ideal for luggage, as you experienced.

Accommodation

The Westin River North is an excellent choice for location — close to the riverwalk, theaters, and dining, making it easy to explore without a car. Being able to leave luggage and explore before check-in is a helpful tip for other travelers.

Food and Dining

Lou Malnati’s at the Wrigley Building — classic Chicago deep dish, good for a must-do experience.
Harry Caray’s — fun, busy spot with lots of local character and memorabilia; great for a casual, lively dinner.
Frontera Grill — an excellent choice for a high-quality, memorable meal with authentic flavors.

Sightseeing & Activities

Architecture river cruise — a highlight, offering insight into the city’s architecture while relaxing along the river.
Navy Pier — a short visit to enjoy the pier atmosphere, watching the college football crowds and festivities.
Walking along the Magnificent Mile and Grant Park — ideal for taking in shops, landmarks, and general city vibe.
Arts in the Dark Parade — a great local event, giving a sense of the community and lively atmosphere.
No Kings March — another fun, busy spectacle that adds local flavor to your itinerary.

Tips & Observations

Chicago weather in October can be surprisingly warm, allowing for short sleeves and outdoor cocktails — always check the daily forecast, but layers are recommended.
Using the L is convenient for airport transfers, but keep in mind elevator conditions if traveling with large luggage.
For short trips, plan activities geographically to minimize walking fatigue, especially if packing sightseeing into a single weekend.
Local festivals and parades can add unexpected fun but may also bring crowds — plan around major events if you prefer quieter sightseeing.

Overall, your weekend seems like a perfect blend of iconic Chicago experiences, good food, and local culture. Your observations about the elevators, weather, and festive events are helpful for future travelers. Returning with family and allowing more time will let you dive even deeper into the city’s offerings.

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