Chicago - First time in Chicago - where to stay and what to do?

My girlfriend and I are going to take a weekend trip (Friday morning to Sunday night) to Chicago in April and could use some advice. We are both in our upper 20s.

1) We are looking for a hotel to stay in that is in a good location. I have some decent corporate rates at the four seasons and the trump building, but a friend recommended that I just go on priceline the day before and grab a hotel in river north for $100 or less. He said they were all good hotels and has done this 40 times in the past 6 months. Corporate rates are nice discounts to regular asking price, but $100 a night just sounds great considering we wont be in the hotel for the majority of the time. I think location and convenience is most important here, and a decent but clean hotel (or better) should do the trick as long as the location is ideal.

2) Dining and nightlife. We both love to do the food and wine thing, so going to a few great restaurants for lunch and dinner will definitely be happening, plus maybe some going out afterwards to bars, etc. Any recommendations?

3) What are some recommendations on things to do here during the day? We are both from NYC so we are used to large cities, and didn't want to spend time on things that are common in NYC. Any particular things to see or do while we are there? I'd like to keep everything convenient and relatively close to the hotel as we have limited time and want to make the most of it.

Thanks!

I would recommend the trump. Can't get any better than that and the location is perfect.

Also, of you have decent weather in April, the trump has a outdoor lounge/bar on the 16th floor. Really cool place to have a drink. Looks north/east/south over the city.

Asking what to do in Chicago for a short weekend is like asking what to do in NYC - there are literally thousands of possibilities. The museums are a big draw but if you visit the ones in NYC you might want something different. Navy Pier (http://www.navypier.com/) is the busiest tourist attraction every year but is super-touristy and the only thing really worth seeing is the view from the far end. The Sears/Willis (http://www.theskydeck.com/) and Hancock Observatories (http://jhochicago.com/en/) offer great views, but I prefer to spend the same amount of money at the Signature Lounge (http://www.signatureroom.com/Signature-Lounge/), where you get the view plus a drink. You could catch a Cubs game (http://www.cubs.com) at Wrigley Field if they are in town, stroll around Millennium Park (http://explorechicago.org/city/en/millennium.html), or go see a play (http://www.broadwayinchicago.com/).

For restaurants, there are a ton of them, ranging from cheap hot dogs to some of the best eats in the world. I personally like to use Metromix (http://chicago.metromix.com/)to find ideas, but I would recommend some deep dish/stuffed pizza (Uno's (http://www.unos.com/), Lou's (http://www.loumalnatis.com/), Gino's East (http://www.ginoseast.com/), Girodano's (http://www.giordanos.com/)), Italian beef (Portillo's, Al's #1), and maybe a nice meal or two. Depending on your cuisine and budget, you might want to make a reservation (http://www.opentable.com/start.aspx?m=3&mn=11) sooner rather than later (you can always cancel it).

If you have specific questions please post them here as there are a lot of Chicago FT'ers. Sorry I am not much help re hotels, except to say there are a lot of them so you probably can snag a last minute deal if you're feeling risky. Good luck with the travel planning!

I'd like to keep everything convenient and relatively close to the hotel as we have limited time and want to make the most of it.

Thanks!

Go to Vegas.

Even though I don't know your budget, here are some food recommendations:

Splurge restaurants:
- Alinea
- Next
- Arun
- Avenues

Great, and not bank-breaking:
- Renzo Piano
- Avec
- Blackbird
- Mana Food Bar
- Hearty Food Bar

Explore our neighborhoods for some great food, too. Like Andersonville, Wicker Park, West Loop, etc.

Enjoy. It's a great city.

Frequent Miler had a great blog post today about his recent trip to Chicago and things to do - http://boardingarea.com/blogs/frequentmiler/2012/03/12/weekend-in-chicago-stuff-to-do/

Also, of you have decent weather in April, the trump has a outdoor lounge/bar on the 16th floor. Really cool place to have a drink. Looks north/east/south over the city.
agree fully with Terrace at Trump http://www.trumphotelcollection.com/chicago/rooftop-restaurants-chicago.php but ONLY if the weather is nice to sit outside.

As far as the Trump hotel overall, whatever:rolleyes:

Chicago's lakefront & numerous parks are such an asset, make sure you take a nice long walk/bike/segway along the lakefront.

A cocktail on top of the Wit hotel at the Roof bar is one of my favorite things to do. Very swanky indeed! Joe's Stone Crab, Hugo's Frog Bar also big favorites but they can be budget busters. Have a drink at The Bar in the Peninsula, it has a wonderful atmosphere. Very sexy.

Stayed at the Hyatt on Martin Luther King Dr. Pretty desolate area, maybe due to the fact that it was a business area. It was only a 10 min. bus ride from the Miracle Mile, so that was nice!

Stayed at the Hyatt on Martin Luther King Dr. Pretty desolate area, maybe due to the fact that it was a business area. It was only a 10 min. bus ride from the Miracle Mile, so that was nice!the area is also the convention area, this Hyatt & the Marriott by UIC/Medical District are two chain hotels to utilize if one must stay at their chain & are looking to save some $, because both properties are removed from the downtown area, they generally are a decent value when downtown properties are too expensive. Plus as you stated, a somewhat short bus or El ride will get one downtown.

Another cheap option is to stay at the numerous nice ORD area hotels & simply take the blue line El downtown but like the OP stated: I have some decent corporate rates at the four seasons and the trump building, but a friend recommended that I just go on priceline the day before and grab a hotel in river north for $100 or less.so I would suggest having a cancelable reservation for the location where you want to be and if Priceline/hotwire offer a great deal, take it, then cancel the other reservation.

If you have decent corporate rates at the Four Seasons or Trump- either one will be good. Get a room with a view if it is not a bank buster.

There is really so much to do in Chicago- maybe narrow down what you are looking for?

A lot of people rave about the Rick Bayless restaurants- and they do have a nice vibe and are very busy- be sure to book in advance or better have your conceirge do it for you.

Enjoy Chicago.

I agree with the suggestions to get out to the neighborhoods - public transportation makes that pretty easy. Some good restaurants outside of the downtown area: Longman & Eagle or Lula Cafe in Logan Square, Irazu in Bucktown, Big Jones and Vincent in Andersonville, Leopold in West Town, Nightwood in Pilsen. Ina's in the West Loop or Meli - downtown and Greektown - have great breakfasts.

As far as bars, it's hard to make recommendations without knowing if you prefer cocktails, beer or wine; a scene of something chilled out. The Wit, as mentioned, is a great all-around option. You might also be interested in Paris Club/Studio Paris, Tasting Room, Aviary, The Violet Hour... in addition to Metromix, check out Time Out Chicago for bars, events and music.

A lot of people rave about the Rick Bayless restaurants- and they do have a nice vibe and are very busy- be sure to book in advance or better have your conceirge do it for you.

I have eaten at both and personally think Frontera Grill (http://www.rickbayless.com/restaurants/grill.html) is a much better option than Topolobampo. The food is excellent and you won't spend near the coin.

I've not been to Xoco (http://www.rickbayless.com/restaurants/xoco.html)but hear it is great, although the wait can be rather long.

I have eaten at both and personally think Frontera Grill (http://www.rickbayless.com/restaurants/grill.html) is a much better option than Topolobampo. The food is excellent and you won't spend near the coin.

I've not been to Xoco (http://www.rickbayless.com/restaurants/xoco.html)but hear it is great, although the wait can be rather long.

I like Frontera Grill as well. Very good.

Xoco my colleagues attempted to go to last week and gave up after 90 minutes.

These are all great ideas, thanks guys.

If architecture interests you, no one has yet mentioned the walking tours given by the Archicenter, or take the el to Oak Park to see the Frank Lloyd Wright Home and Studio.

Lots of good suggestions above.

To get the real Gold Coast/Lincoln Park flavor, I suggest a not too long walk starting from Division and North Dearborn (just north of the Michigan Ave. shopping area). Walk north on Dearborn 4 blocks through some of the finest architecture in the world (lots to see in the blocks east and west of Dearborn too) until you hit Lincoln Park at North Avenue. Cross North into the Park and continue to walk toward the boating pond and the Zoo. Visit the Zoo (free) and visit the conservatory (hot house tropical collection) just north and west of the Zoo. Then cut over to Clark Street just west of the Part and walk a few blocks further north to Diversey for shopping and general atmosphere. Take a cab home. Or, just hop the #22 Clark St. bus.

You'll know a lot more about Chicago after this walk.

And, don't forget to hit a blues club. Check the Reader for listings. http://www.chicagoreader.com/
Kingston Mines is a good place to start. http://kingstonmines.com/


PS Don't even think about staying by the airport. Would you stay in Queens if you wanted to see Manhattan? North Michigan Ave. is where to be for a tourist.

Would you stay in Queens if you wanted to see Manhattan?

Near Silvercup? Affirmative.