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Posted

decided to risk our lives 😆🙄...

headed to Chicago in two weeks for first time! 😊

combining with a short road trip to Wisconsin to visit niece, but will have 4 nights. staying near Millinneum Park downtown. 

will be perusing recent pages for food recs. thought we'd do a boat tour, basically see what TripAdvisor top 10 things to do are.

might try a show...any suggestions on theaters?

2.5 hours to Madison, hope it's a pretty drive this time of year...hotel in Madison near the capitol on the isthmus is as much as d/t Chicago! 😮

 

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Posted
decided to risk our lives ...
headed to Chicago in two weeks for first time!
combining with a short road trip to Wisconsin to visit niece, but will have 4 nights. staying near Millinneum Park downtown. 
will be perusing recent pages for food recs. thought we'd do a boat tour, basically see what TripAdvisor top 10 things to do are.
might try a show...any suggestions on theaters?
2.5 hours to Madison, hope it's a pretty drive this time of year...hotel in Madison near the capitol on the isthmus is as much as d/t Chicago!
 

Boat tour is a must for a first timer, explains a lot about riverfront access and setbacks and why Chicago architecture is unique.

If you’re staying near Millennium Park, I can recommend Gage as a nice place to eat. Especially if the weather is nice and you can sit outside overlooking Michigan ave and the park.

Wildberry pancakes is just down the street near Michigan and Randolph and is an awesome breakfast place.
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Posted

I have a quick trip to one of our offices in Naperville, but I should be able to get away for one night close to the city before I head out of Midway.

I would love to stay somewhere on the affordable side that is easy to get to the airport and close to a cool area downtown to eat and walk around and find a dispensary.

I'll probably be back again within a year or two, but this is my first time.  I will try and make a late boat tour, but that might need to wait until next trip.  

Any recs on a hotel or neighborhood that would give me a taste of the city and a quick trip to the airport the next morning?

Posted

If you can swing the commute of just over an hour from Naperville to a hotel in River North and then another hour in the morning to the Airport, that will give you a great feel for the City. And bonus if you can get a dusk or evening boat tour.

I’ve stayed at the W on lakeshore drive, the Marriott Marquis in a high NE corner suite with city and lake views, and the Hotel Chicago (Autograph) by River North and they all had good views but weren’t cheap. The latter used to be the office complex part of the corncob buildings and is a block from the river and walking distance to some great restaurants. Neat hotel with a muted, contemporary vibe.

Otherwise I’m crashing at my daughter’s 5th story walkup in Andersonville that I suspect is an old convent, which is a cool neighborhood vibe with lots of good old school cool restaurants and a shitload of lesbians. It really depends on the vibe you want.

My wife spent her adolescence in Naperville so she loves going back to the old neighborhood.

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Posted
On 10/7/2025 at 5:59 PM, mchookem said:

decided to risk our lives 😆🙄...

headed to Chicago in two weeks for first time! 😊

combining with a short road trip to Wisconsin to visit niece, but will have 4 nights. staying near Millinneum Park downtown. 

will be perusing recent pages for food recs. thought we'd do a boat tour, basically see what TripAdvisor top 10 things to do are.

might try a show...any suggestions on theaters?

2.5 hours to Madison, hope it's a pretty drive this time of year...hotel in Madison near the capitol on the isthmus is as much as d/t Chicago! 😮

 

As many have noted, boat tour is great. Another option: we rented a pontoon boat and just did our own thing. We had a total of 8 people. Had a lot of fun just cruising around on the water.

Posted
On 10/8/2025 at 3:43 PM, Chips O'Toole said:

I have a quick trip to one of our offices in Naperville, but I should be able to get away for one night close to the city before I head out of Midway.

I would love to stay somewhere on the affordable side that is easy to get to the airport and close to a cool area downtown to eat and walk around and find a dispensary.

I'll probably be back again within a year or two, but this is my first time.  I will try and make a late boat tour, but that might need to wait until next trip.  

Any recs on a hotel or neighborhood that would give me a taste of the city and a quick trip to the airport the next morning?

"easy to get to the airport" and "affordable" are the wild cards here. If you're cool taking the train to the airport, get a hotel near the orange line, which runs through the loop downtown. It goes right to Midway, and then it's about a quarter mile walk from the train to security. If you're gonna take a taxi or a ride share, it doesn't matter where you stay (from a convenience perspective), but just know the neighborhoods get rougher as you go further south and west. As far as the neighborhoods to stay at look into river north, the loop, magnificent mile, west loop, streeterville, or a little further out would be old town and gold coast. You could do south loop too, but I wouldn't go south or west of south loop/west loop. Anything north or west of that you're into neighborhoods, which could also check most of your boxes, but obviously not gonna have easy access to the downtown shit. 

 

 

 

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