highlanderfil

My girlfriend's birthday is coming up in July and we were looking to go to Chicago (would be her first time). We'd drive in from Lansing, MI on the 8th of July (Wednesday), stay two nights, then possibly go to Milwaukee and then maybe Holland, MI on the way back on Saturday/Sunday. With that in mind, I'm looking to burn some of my rewards points, but wanted to maximize value since the easy solution (2 free IHG nights) won't really get us our money's worth (the most expensive IHG property is $249 for those dates, so I'd rather save those nights for when I/we inevitably go to NYC or L.A. later this year). Unless, of course, any of those properties are absolutely awesome, in which case they'd fall back into play.

So, here are my point balances (give or take):
- Amex: 80K
- Chase: 110K
- Marriott: 110K
- IHG: 300K + 2 free nights
- Hhonors: 15K

What properties/redemption/transfer strategies would you recommend? Proximity to the sights, parking and comfortable beds are really our only requirements.

Thanks!

IRep312

Anytime I went into the city, I always stayed at the Renaissance on State & Wacker. Beautiful hotel, great location and great views from the higher floor rooms.

glg

Unless you have a specific sight to see that requires a car (skip Milwaukee on this trip, it's a fun city worth its own weekend and rushing up for one day isn't worth it), you're better off trying not to bring your car into the city. Parking rates downtown are crazy, and even higher at the hotels. I would guess you'd be better off leaving your car in South Bend and taking the South Shore train into the city. Maybe some other Indianans or Michiganders can weigh in on that option.

highlanderfil

Yeah, actually the Amtrak might be the better option. I saw some of the parking rates - NYC is freakin' cheaper!

knoebelsPT

This is a generally a good choice, but I believe is going through a major renovation right now. The common areas are ripped up and I'm not sure about the rooms

The Wit, which is a Hilton property, is across the street and has a hipper vibe if that's your thing.

The InterContinental Michigan Avenue is very central and would work if you wanted to use your free night certificates.

I've never been all that impressed by the Marriott options. The Blackstone on South Michigan is an exception but may be too far south depending on what sights you wanted to see.

highlanderfil

Not enough value to plonk down the reward nights - IC is only $250. My company rate can get me around $135/night on HI Miracle Mile or the Chicago Downtown Autograph (but the latter only on weekdays - weekends is almost $500), so I may end up doing that. Overall, not really seeing good redemption values, tbh.

The Wit is nice but freakishly expensive.

humali

What's the rate of parking?? I'm going there next month too. TIA

highlanderfil

$60-70/night at hotels isn't out of the realm of possibility.

glg

That is the high end of things. It's most likely valet and will include in/out privileges. If you just want to park you can find better than that (probably more like $25-30/day) for self park without in/out. On a weekend, maybe even cheaper, depending on how far you're willing to go, etc. The other piece of it is that traffic can be just awful depending on when you're coming in, especially on a Thursday or Friday afternoon and if you try to drive anywhere on the weekend it can be bad too. If you're hitting the "touristy" stuff around the Loop and Michigan Ave, you won't even want the car.

highlanderfil

Now, the question is - is there enough to do for a four-day trip? We're not the going out, clubbing all night types. I wouldn't have a problem filling up such a trip in NYC, but not sure about Chicago. Advice?

chgoeditor

I have to admit, I laughed when I read this question. I've lived in Chicago for 25+ years. I've traveled a lot and feel that a week is often insufficient to see a world-class city such as London, Rome, Paris, Hong Kong, Tokyo, Washington DC, New York, Boston, etc. And I'd include Chicago in that list. No offense, but unless you're a boring person with a very limited set of interests you'll probably feel that four days was far too little time to fully explore and enjoy Chicago.

If you want to share some of your interests, then we can help you come up with an itinerary. And if you haven't already, read the un-tourist's guide to Chicago thread.

highlanderfil

I'm an extremely boring person. Problem is, I'm obviously biasing it towards myself rather than the gf, since I've been to the city a few times already and am a little bit familiar with the sights.

Interests, let's see (yep, I broke my own rule of listing them straight away, mea culpa):

- sports (checked that box)
- zoos (on the list)
- museums (more her thing than mine)
- good food (more my thing than hers)
- all things automotive/technology-related (way more mine than hers)

Problem is, most of the things I named are rather generic and certainly not specific to Chicago. What I was looking for, more than anything, are certain Chicago-specific attractions that are of the cannot-miss variety. I'm definitely not one of those people who comes to NYC and gets bored after a day because there's nothing more to Manhattan than skyscrapers - I genuinely asked because, apart from the perfunctory touristy stuff that I've done (Hancock Tower, etc), all I've done was walk around the city and I found it to be very compact (much more so than NYC, hence the comparison). So on this trip, at least for me, it would be good to know how deep to dig and where to get beyond first impressions.

Also, I'm sure, also, that there are plenty of things to do outside the city, but if we do end up taking the train, those will be a little bit less accessible.

Thanks for the tip about the guide, I will definitely give it a read.

chgoeditor

So first things first: You'll be in town during Taste of Chicago, which I personally think is a gluttonous, disgusting waste of money -- and I personally spend a lot of money on restaurants. The problem is that it's not a truly representative "taste" of Chicago's dining scene, so if you're more of a foodie, you'll want to skip it. Instead, check out LTHforum.com's list of "great neighborhood restaurants" and visit some of the dining spots that make Chicago great. (Or, check out the James Beard Award winners or Michelin-starred restaurants.) And if your girlfriend really wants to go to Taste of Chicago, we won't hold it against you.

Chicago's a great city for neighborhood festivals. The Square Roots Fest that weekend and is held in Lincoln Square -- a neighborhood known for its German restaurants. They'll have more than 30 regional craft breweries in attendance, and the fest supports a local school of folk music, so you can expect some good performances. There's also a burger fest and a BBQ fest that weekend. Check Time Out Chicago's events listings.

The Chicago-Mackinac boat race -- the longest fresh-water race in the world, I believe -- kicks off that Saturday at about noon. Normally I'd never suggest going to Navy Pier on a Chicago weekend, but it's a great vantage spot from which to see the boats. Alternately, a trip to the top of the John Hancock (another thing I'd typically never suggest will give you another cool view of the sailors setting off).

If you're interested in seeing Chicago's main sights through a different lens than your average sightseeing tour, consider booking one or several excursions with the Chicago Architectural Foundation. You can choose tours offered by boat, L train, trolley, bus, walking...you name it.

Since Chicago's a fantastic lakefront and riverfront city, you owe it to yourself to do something on the water. The CAF's river architectural tour is a favorite, but if you'd prefer something out on the lake, I'd suggest doing that on a day other than Saturday, since the Chicago-Mac race will cause the lakefront to be a bit congested.

If you go to the Lincoln Park Zoo, be sure to also check out the Lincoln Park Conservatory as well as the Alfred Caldwell Lily Pool. The later, in particular, is a hidden gem in Chicago. I'd suggest heading to the Zoo on Saturday morning, when Green City Market -- the city's best farmer's market -- takes place adjacent to the zoo. There are some fantastic prepared food vendors there so it can serve as breakfast or lunch, and there's often a top-name chef doing cooking demos. After the zoo, head to the top of the Hotel Lincoln (across the street) for a drink on the rooftop.

Chicago's known for its world-class theater. You might check into the Goodman, Steppenwolf and Lookingglass, among others, to see if there's anything which catches your fancy. (We also have a ton of Broadway-style productions, but I prefer the smaller theater companies.)

gretchendz

Since she likes museums and you like automotive/technology, I'd suggest Museum of Science and Industry. Among many other things,the captured submarine exhibit is fantastic.

highlanderfil

I'm actually the more adventurous eater of the two of us, but I'm not a giant fan of restaurant weeks myself. So, good to know and definitely will check out the list.
German restaurants, you say... We're not really drinkers (her not at all, me almost not at all), so the beer aspect isn't as interesting, but the food and performances should be.It might be something to check out, but not really focus on (though I'm just speaking for myself here).Yes! This is perfect.Yep, both of us do like the prospect of "doing something on the water". The Thursday would be the perfect day for it, I suspect, if the weather obliges.Will do. This is definitely useful. And I do like farmers' markets.I suspect she will be much more interested than me as she's in East Lansing now, having moved from Russia as an avid theater-goer, and has been complaining about the dearth of performances in MI.