We have our flights booked and now I'm ready to start the serious planning / booking. We fly into Chicago on December 26th at about 3.30pm. We have an early morning flight on December 27th to Yellowstone. We fly back to Chicago on January 1st for 3 nights before flying home.
I have LOTS of questions and as I'm at the very start of our planning please forgive any 'silly' questions. Also, we only ever overnighted at a hotel near the airport (Holiday Inn Select on Higgins Road in Rosemont) and have never actually seen any of Chicago.

For ease I'm going to number my questions:
1. For the night of the 26th I'm thinking we should stay near the airport - maybe the Holiday Inn Select Rosemont as we thought that it was a really nice hotel and the food in the bar was good (we ate lunch there) OR any other suggestions?

2. Should we just opt for a 'night in' on the 26th or would ie be relatively easy to go somewhere without rushing?

3. When we get back to Chicago on the 1st of January what location should we look at staying in. I see a lot of refferences for the Magnificent Mile - is this the best area to base ourselves?

4. I have been looking on Tripadvisor for hotels and I see the Amalfi rating pretty good. They also offer a continental breakfast and evening coctails and the price seems pretty good. I also have been looking at the Omni and the Conrad - would it be worth the extra for one of these or does anyone have any other recommendations? While we will be in Yellowstone accomodations will be pretty basic so we're looking for something 'nice' and also value for money. We don't mind paying a little extra if it's worth it.

5. We would like to go to at least one show / performance. We really like the Cirque Du Soleil Shows in Vegas as well as The Blue Man Group and we also enjoyed the Christmas Spectacular show (can't remember the correct name) in NY last year. I see that there is a show called Cirque Jungle Dreams playing while we are there. I know it's not the same company as the Cirque shows in Vegas etc but it looks interesting - has anyone heard anything about it?

6.Any other shows, acts recommended??

7.We definately want to go to Navy Pier and Millenium Park. we're not hugely into museums so we're not sure what else we should go to see - any other suggestions?

8. SHOPPING - When we went to Boston last year we had a filed day in Filene's Basement. I have read that there is a Filene's Basement in Chicago - does anyone know anything about it - good bad?? Also, any other recommendations for the best shopping (bearing in mind we are coming from Ireland so most places will be a LOT cheaper than at home but we still want to get the best value).

Apologies for so many questions all at once - hope no-one minds.

Thanks for all advice!

Hi. I was just in Chicago this weekend, so I can answer a couple of your questions anyway.

If you arrive on time, there's no reason you can't go into the city for the evening of the 26th. 3:30 until bedtime is a long time to spend in a motel room at the airport! On the other hand, it will actually be much later "Ireland time", so you may be tired when you arrive. If you do decide to go into the city, you can take a cab or the "el" (train). I don't know the cost, because we always take the "el". which is about $2.00.

The Magnificient Mile is like Fifth Avenue. I don't know the Amalfi, and not sure where the Conrad is located, but the Omni is ON Michigan Avenue. We always stay on or near Michigan Avenue because it's so centrally located and convenient.

The Magnificant Mile is the stretch of Michigan Avenue from the river north to Oak Street. It has the highest concentration of stores and hotels. You'll find everything from Burbery, Saks and Cartier to Marshall's, Filene's Basement and H&M.

Navy Pier is about a mile east of the Mag Mile. You can catch the free trolley at Michigan and Grand.

If you want to go shopping, also head to The Loop and spend some time at Marshall Field's/Macy's on State Street. The Loop is the center of the business district and in addition to Macy's, you'll find another Filene's Basement, TJ Maxx, Nordstrom Rack and Old Navy.

The major theatres are also in the loop. Wicked is playing at the Ford Center. Phantom will be at the Palace through January 5 and Jersey Boys will be at the LaSalle Bank Theatre. For other theatres, check www.chicagoplays.com.

Either area would be fine for a hotel. The Mag Mile is probably a bit more lively at night because the Loop has more offices.

I would suggest leaning towards more indoor activities. Chicago in January can be pretty brutal, the last few years, not so bad, but it will be cold
The Art Institute is a must see, even if you are not a museum goer. I would skip Navy Pier. Millenium Park will be pretty, they'll have an ice skating rink. Macy's on State (formally Marshall Field's) will still have it's windows decorated for the holidays.

I have had very good luck with getting 4 star hotels cheap in Chicago using Priceline. I have stayed in both the Loop area and the Mag Mile and I actually prefer the Loop because it's closer to the elevated rail line (the El) coming from and going to the airport with baggage.

Having said that though, it was worth the walk across the river to stay at the funky House of Blues hotel - but that was not January!!!!

Plan for cold weather! Chicago is on a big lake and can be brutal in the winter! You will want a hat, gloves and scarf and the wind whipping around the buildings can literally make you cry!!!!

It's easy to ride the El back and forth to the airport so if your hotel is near the line, going downtown on the 26th will be no problem.

I have heard many recommendations for Wicked but haven't seen it myself yet. I enjoyed the Shedd aquarium and the Field Museum of Natural History. These are not the typical museums so might be worth a look. I have also enjoyed night time hockey games - which might be interesting if you have never been to an NHL game and the BlackHawks are in town. You would find a lot of people to talk to there!

I like the Filene's basement on State Street south of the river. It is under a TJ Maxx and across the street from a Nordstrom's Rack. I always find treasures in those places!

Dress warm and you will have a blast! (and hopefully not the mother of all hangovers since the bars stay open LATE!)

I would opt for a half day at the Shedd Aquarium-Chicago's top attraction and a wonderful place to view the skyline and Lake Michigan in the comfort of heat.You can eat lunch in either the food court in the lower level or in the Marriott catered diningroom upstairs for a beautiful sit down lunch (about $7-10 ).The aquarium is not a stuffy place and the oceanarium with the dolphin show and belugas is neat. The new Wild Reef along with Amazon Rising will make you feel like you have traveled the world.I think that you would really enjoy the Shedd!

I agree with the poster who advised you to skip Navy Pier-- (in my opinion) it's touristy in the worst way--and in the winter, the one appeal, being out on the lake, is pretty much gone. At that point, it's just an overpriced mall with crappy stores and mediocre-to-crappy food. Having said that, Navy Pier IS host to one of the world's best Shakespeare theaters, Chicago Shakespeare Theater. I can highly recommend taking in a show there (the bulk of productions are Shakespeare works, but not always).

I would get out of downtown for an afternoon and into one of the neighborhoods... Wicker Park is a good one (more trendy/funky), as is Lincoln Park (more upscale)... tons of good restaurants, cafes, and boutiques, if you want shopping.

I have to agree about Navy Pier -- I just don't get the appeal (and honestly, neither did my kids when they were there, and they were 11 and 13 at the time).

Thanks so much for all the great replies.

I have found a great rate ($420 for Jan 1st to 4th) through hotels.com for the Amalfi. I have e-mailed the hotel directly to see if they can match the rate and if so I will book it as a 'back-up' hotel. Hopefully I will be able to pick up a deal on Hotwire or Priceline nearer the date.

Citylghts - thanks for the clarification on where the Magnificent Mile is! The Amalfi isn't located directly on it but it looks like it's only a block or so away.

I am going to go ahead an book the Holiday Inn Select in Rosemont for our 'layover' and plan to just take it easy that night. After all, we have a 7am flight the next morning. This brings me to the question - what time should we plan to be in the airport for this flight??? I've heard that ORD can be pretty hectic!

Thanks on the tip to skip Navy Pier - it seems to be the consensus. We will wrap up for Millenium Park - we have been to NY and Boston in Dec / Jan - will temperatures in Chicago be similar to what we experienced there or will it be colder? Should I plan on a long coat or would a shorter fleecelined jacked be OK?
Re the hockey game recommendation dmdevl, is it difficult to get hold of tickets?? We have never been to a hockey game and it sounds like it might be a lot of fun!

I'm still 'researching' so I'm sure I'll be back with lots more questions once I've got my head around things a bit better.

Thanks again everyone for your replies!
Imelda

I agree with your decision to skip Navy Pier. I like it in the summer to just sit at the end, sipping a tall cool one and watching the boats, but in January, nothing there.

I think your short coat with layers would be fine. If it were me and I was walking around in Chicago in January, I would bring long johns to go under my jeans or slacks.

One thing I always suggest is the 96th floor of the Hancock Building for drinks at the Signature Lounge. Lovely views of the Chicago skyline and Lake Michigan. Ask for a window seat.

Weather will likely be similar to Boston or NY-- but check before you come, might be 45 degrees (F), might be minus 10... more likely in the 20s or 30s though.

Hockey tickets should be very easy to get. The team is bad, and management has done a great job of alienating its fans-- so there's not a lot of interest in the team. Not a ringing endorsement, I know! That said, it would be a fun way to spend an evening. If the Bulls are in town, maybe see what those tickets would run you... it would probably be a better game, and a better Chicago sports experience!

For shows, Phantom of the Opera is in town until Jan 5. It is at the Cadillac Palace Theatre Downtown. Not as good as seeing it at the Chicago Opera House (where it played many years ago), but if you are a
Phantom fan......

Thanks all for your help!
Shorter fleece lined jacket it is then and I already have those long johns so they'll be going in too.

Maybe the hockey game mightn't be the best idea, especially when it would be our first game - would prefer a bit of hype around it. I will look into the Bulls tickets instead.

Thanks for the tip on the Phantom betsyatl but I'm afraid I can't get hubby to go to these type of shows ... I know, I know, they're fantastic shows but he's just not into them.
I have been looking at the show Hephaestus, either that or the Cirque Dreams one but I still have to do a bit more 'looking'.

Thanks agiain for everyones help!

Dear OnlyMeOirish,

As a hockey fan, I would just like to encourage you to reconsider attending an ice hockey game. This year the Blackhawks have two first round draft picks who will very likely be in the lineup and are absolutely astounding people at training camp right now. Yes, the team has been bad for the last few years...OK, maybe longer than that, but I'd certainly not rule it out as an option, and you will likely not have trouble getting tickets closer to the time of your trip.

Their Web site is: http://blackhawks.nhl.com/index.html - you can always check in and see if they are doing well or not and make your decision.

Slightly further out of the way, you could also check out the Chicago Wolves, a minor-league team just one level below the National Hockey League, which would be more affordable and still loads of fun: http://www.chicagowolves.com/main/

A Bulls game would be great, too, of course...I just had to get my hockey plug in!

Hope you have a great trip!!