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College Reunion... Hotel, Food, & Day/Night activities...

New York
Level Contributor
140 posts
12 reviews
College Reunion... Hotel, Food, & Day/Night activities...

Hi All - myself and 3 of my college friends have decided to meet up in the city of Chicago and have some fun. This will be the first time in 10 years we are all together again. We are planning to arrive in town on Friday and leaving Sunday. We are 33 & 34 years of age and are in need of advice on the following:

Where to stay... we all travel a bunch and we all like the finer things in life so we are looking for a more upscale hotel reasonably priced that is centrally located to top quality restaurants and bars/nightclubs. We will not have our own transportation.

Where to eat... we all love great food so a restaurant that offers an extensive menu of top quality cuisine to satisfy all would be best for us.

Daytime fun... We would like to see the city of Chicago during the day since most of us haven't been so something fun for the group would be preferred... boat tour... hop on hop off bus tour...

I look forward to your responses / help in planning this trip. Thanks in advance.

Destination Expert
for Seven Mile Beach, East End
Level Contributor
6,735 posts
2 reviews
1. Re: College Reunion... Hotel, Food, & Day/Night activities...

As everybody's idea of finer things is subjective a budget would be helpful.


Destination Expert
for Chicago, Illinois
Level Contributor
57,835 posts
67 reviews
2. Re: College Reunion... Hotel, Food, & Day/Night activities...

www.chicagoreader.com and www.chicagomag.com for the current dining and entertainment scene.

www.choosechicago.com for ideas of things to see/do here. Chekc the calendar for special events.

"upscale hotel reasonably priced" - hotel rates here run all over the place. Chicago is also a convention destination. Check out availability and prices at www.booking.com or similar site to see what's available within your price-point.

Level Contributor
1,554 posts
9 reviews
3. Re: College Reunion... Hotel, Food, & Day/Night activities...

Also when are you coming in as that will affect advice on what to do during the day. Winter activities vs. summer activities, etc. For food - check out the West Loop restaurants.

New York
Level Contributor
140 posts
12 reviews
4. Re: College Reunion... Hotel, Food, & Day/Night activities...

No more than $300 per night for hotel accommodations. Traveling either last weekend of April or first weekend of May 2016.

Edited: 11 September 2015, 18:00
Chicago, Illinois
Destination Expert
for Train Travel
Level Contributor
18,476 posts
140 reviews
5. Re: College Reunion... Hotel, Food, & Day/Night activities...

Well, You're from New York so you understand the $300 per night isn't going to get you the finer hotels. ...close that time of year but not a winner. There are no large conventions in town to raise the room rate. The best hotels in your price range for that time of year seem to be (www.hotels.com) The Virgin Hotel, any of the Kimpton hotels, The Drake, Marriott Magnificent Mile, Soffitel, Godfrey... In the suites category, The Embassy Suites (there are two), Courtyard, Homewood Suites, Hilton Garden Inn.

You might want to do some searching for a hotel in River North. Beware of hotels costing less than $200 per night.

Chicago, Illinois
Level Contributor
2,134 posts
284 reviews
6. Re: College Reunion... Hotel, Food, & Day/Night activities...

Start by looking at kayak.com and see how your budget matches up with hotel prices for those weekends. Check the River North/Mag Mile areas. Those areas are centrally located and the best option for tourists who want to be in the middle of the action while also having access to public transportation/Uber/cabs.

What kind of food are you interested in? Chicago is obviously more than hot dogs and pizza. Budget? Check opentable.com and peruse the "Best of Chicago" lists which breakdown top restaurants by cuisine/atmosphere/etc.

You can also search this forum and the Top Questions About Chicago list to get you started. Let us know if more specific questions arise as you research. Sounds like a fun trip... have a great time.

Chicago, Illinois
Level Contributor
4,452 posts
82 reviews
7. Re: College Reunion... Hotel, Food, & Day/Night activities...

For daytime fun, the boat tours and / or HOHO bus tours are good options. Boat tours will be starting up around that time, so options might be limited to daytime only (which fits your plans). You shouldn't need to worry about buying tickets ahead of time, so play it by ear according to the weather when you visit. That time of year, we can have just about anything.

You should definitely consider setting up a Chicago Greeter tour, these are free tours and can be customized to your tastes. Website: http://chicagogreeter.com/greeter-visits/

Regarding food, the Michelin Guide could be a nice place to start: choosechicago.com/articles/…

Rensselaer, Indiana
Level Contributor
9,121 posts
8. Re: College Reunion... Hotel, Food, & Day/Night activities...

The tip-top quality restaurants will be in the vicinity of $250 to ???? pp. Is that within your dining budget? Or is it more modest? Also, those types of eating establishments usually entail a full evening's dining experience, being several courses. If you were planning on going to the theatre, for live music, or other entertainment, you'd have a conflict.

Depending on the weather, the boat tours may not yet be operating in late April 2016. Early May might be more likely.

Little Rock...
Level Contributor
3,437 posts
59 reviews
9. Re: College Reunion... Hotel, Food, & Day/Night activities...

Hotel room budget $300 each or are you for planning on staying 4 in one room and only spending $300 total?

If each, and you stay 2 per room, 600 / night will get you a nice room during all but peak times.

Also, what type of activities do you enjoy? I don't think it's been determined if you are four guys, four girls, or a mix, but but if you outlined some things you like to do or things you don't want to do (shopping architectural tours, whichever) you'll get better advice.

10. Re: College Reunion... Hotel, Food, & Day/Night activities...

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