Q re: driving and staying overnight in Chicago

MirandaHobbes

When you drive to Chicago, how long does it take? Do you take the Milwaukee route or the Madison route? We're taking a road trip to Michigan and were planning on sleeping near chicago. But looking at Priceline, we think we can get a decent hotel semi-close to the city for $50 and maybe take the train downtown and make the most of the night. In the alternative, we would like to find a nice area that has shopping and restaurants nearby (walkable). Hotwire shows a bazillion neighborhoods/suburbs though, and I'm not familier with any of them, and I can't tell if any of them have a train station nearby. Can you give a shout out to neighborhoods/suburbs that you know are nice, or having shopping or access to trains? We could always stay near O'Hare which is obviously on the blue line, but some of the cheaper hotwire hotels are $34 in places like Itasca which I've never heard of. Thanks!

mbgreenwalt

We drove there last year and took the Madison route.  It took about 8 hours.  Whatever you do don't end up trying to drive into the city during rush hour.  It took us 80 minutes to go 10 miles.  I'm no help w/ where to stay.  We stayed at the Omni Hotel on Michigan Ave.

wittyschaffy

I was just there 2 weeks ago and it took us 6 hours to drive via Madison from St. Paul.  We opted to take the non-toll route home through Milwaukee and it was only like 30 minutes more.  Depending on when you're going to be there, you might get lucky using priceline "name your own price" stuff for a hotel downtown.  We stayed downtown on a Sunday night so I searched for a 4 star hotel downtown for $70.  We got matched to the Hyatt, just across the river from the Wrigley Building and walkable to the Magnificent Mile.  Couldn't have been happier.

huwehotaling

The Madison route is much quicker, about 6 hours.  If you stay close to the Midway airport the train is pretty quick into the city (about 30 mins).  O'Hare is a little farther away so the train takes about 45min.

ElizabethD

I love Chicago!  I"ve done every combination since I have friends there, but also did a wedding there twice and stayed in a hotel with a car.

Honestly, if you're road tripping and this is just a pit-stop to keep on going, you may want to just say, it's worth $30 to park overnight and DRIVE INTO the city and stay at the hotel.  Then you can drink, have fun, walk back to your hotel and not deal with train schedules, tokens, ending up in a bad neighborhood (or REALLY FAR AWAY...)  The Midway airport is not a great part of town.

And then in the AM you just get in your car and go!  No more train schedules, taking 30 minutes to potentially go "backwards" then drive the 30 minutes forward to then keep on going to Michigan.

Have a blast!! (Oh, and if you did hotwire, you can go to the local chicago boards, tell them the areas from Hotwire,'s little map thingie they do... tell them you want to be downtown to have fun, and they'll tell you exactly which ones, if any, to avoid.

Elizabeth81

We took the Madison route last time we were there and it took us about 7 hrs, with about 3 stops along the way for gas/food/bathroom/walking around.

ETA: We stayed in the Loop area at the Club Quarters and the rooms were a bit small but it was a fantastic location and a great price. Also a very nice hotel.

ilovebijou

We've stayed at the Conrad Hotel and Affinia. Both were in the Magnificent Mile area and very nice. I'd definitely stay at either again.

MirandaHobbes

Thanks ladies! Looks like I have to go the Milwaukee route- our first night "layover" hotel night is in Skokie at a nice  Doubletree. Free parking and across the street from a big mall so we'll just stay in the burbs that night. Our last night we're staying downtown (priceline Hilton downtown- hoot!) and doing the whole downtown scene. Best of both worlds! Hopefully I won't get too hammered by traffic, but the Doubletree is very close to I-94.

Mrs. Sarah&Micah

We were just in Chicago about a month ago. We always end up staying by the airport and just taking the blueline train into the city. Last time we stayed at the Aloft hotel and it was really nice and we liked it. The train does take about 20-30 minutes to get downtown, but it's super easy to navigate and we end up getting the 3 day train passes which also includes bus transportation as well downtown. We did try to drive downtown one day and traffic was horrible and it ended up taking an hour and half to get there and to find parking- not to mention parking was outrageously priced. If I were you, I would just stay at the airport and take the train- SO much easier and less stressful.