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Where to stay in Chicago?

I'm planning to do road trip from Columbus, OH to Chicago - what hotels (great value, clean, good beds) do you recommend to stay if we only have 2-3 days to explore the city? Would it be better to stay centrally or somewhere outside the city center since we have a car? 

5 Answers

top answer by
Melissa from St. John's, Newfoundland

I stayed a few nights at the Wyndham Blake Chicago on S Dearborn St (at Congress) when I was in town back in 2011. I thought the location was great and the prices were very reasonable at around $115/night.

Mentioned in this answer:

  1. Wyndham Blake Chicago (hotel)
4 thankscomments (1)

answered by
Ted from Chicago

It will probably cost you $150-$250 a night to stay in the city at a decent hotel. Hotels at O'Hare airport are a little cheaper running $80-$150, which is a half hour from downtown. Nice thing about O'Hare and suburban locations is you should be able to park for free. City locations would probably tack on an extra $20.00 a night for parking.  It depends on your budget whether you want to save $50+ bucks a night and be away from the city or splurge and stay downtown. I would recommend staying a night downtown and a night in the suburbs. You get the full downtown experience by staying overnight in the city. Hotel Monaco is $139.00 a night, which is not too bad for the city.

Mentioned in this answer:

  1. Hotel Monaco (hotel)
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answered by
Debbie from San Francisco

I would say that it depends on your allotted budget for the trip.  When I travel, I always try to stay in the city proper when I can afford it, but am willing to stay in one of the suburbs if it's more affordable.  If you were flying in, I'd more likely suggest staying in the city, but since you'll have a car, if you'd like to save a few bucks, you could stay in surrounding cities or the more residential parts of the city. 

One thing that you should keep in mind is that it's very difficult to find parking in downtown Chicago, around the Millennium Park area, and that it can be expensive.  I remember I had to pay $26 for half day parking around there.  My ideal situation would be that I stay at a place in a residential neighborhood in the city and take public transportation/cabs around to explore.

So the last time I road tripped to Chicago, I was fresh out of high school and went the suburbs-route.  One thing that I remember, though, is that I ate at an awesome vegan diner called The Chicago Diner and that it was relatively more easy to find parking around there.  I actually just looked them up and the Villa Toscana is very close to it and according netizens, has parking and is affordable, so maybe you can look into that.

Have fun :)  I love road trips!

Mentioned in this answer:

  1. Millennium Park (attraction)
  2. The Chicago Diner (restaurant)
  3. Villa Toscana (hotel)
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answered first by
Kenin from Florida

Whenever we road trip we end up staying in a suburb of a major city. Typically the inner-city hotels cost more than the outskirts, plus they charge you for parking on top of the already higher rate. 

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answered by
Jordin from Chicago

Hotels in the city or around the city is where you want to stay. Anything near the suburbs will leave you in traffic for longer than your trip itself! I live in Aurora (a suburb an hour away from the city) and I've stayed at the Sheraton Chicago Hotel & Towers (expensive hotel near the lake) and at the MileNorth, A Chicago Hotel (average expense for Chicago) which is right behind where the touristy areas are. Staying downtown would make your trip better because everything is within walking distance (depending on your health) I've walked across the city and back so many times I didn't even notice I was walking in circles because there's so much to look at. But since you have a car, make sure to google the places you want to go so you can drive there. Traffic is CRAZY and I refuse to drive in the city but if you're tight for cash, drive around (even though it might take longer than walking on a weekend) I recommend Rockit Bar & Grill or Schubas for lunch.

Mentioned in this answer:

  1. Sheraton Chicago Hotel & Towers (hotel)
  2. MileNorth, A Chicago Hotel (hotel)
  3. Rockit Bar & Grill (restaurant)
  4. Schubas (attraction)
1 thankscomments (1)

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