Chicago--car rental

[dodojojo]

Chicago MMMers, advice needed on renting a car.  I plan to visit this summer for less than a week.  During that week, I'd like to rent a car and drive to Kentucky for a couple of days.

The advice I got from one Chicagoan was that it was more expensive to rent from O'Hare than from a city location.  I think it's likely true that it would cheaper to rent in Chicago--but out in the suburbs.  If I'm staying in or close to the Loop, wouldn't rental prices be higher?

I'm also trying to figure out the logistics of the Kentucky trip.  I've looked in to flying to Kentucky from Chicago and flying home--buying a multi-city ticket basically.  This jacks up the cost but takes out the car rental issue.  Aside from the cost, I do not favor this option as the KY airport is small and I do not like the little planes.

My initial plan is to go to Chicago, do the touristy stuff, rent a car and drive down to KY and then drive back to O'Hare and board plane.  This would necessitate paying an extra fee if I'm picking up the car in the city and dropping off at the airport.

Anyhoo, any word of advice to simplify the logistics and lower the cost would be appreciated.

Argh, travel planning--this is why stay-cations are so appealing!

[SurlyTroll]

There is a Dollar rental car in the loop. I've used them a couple times. Relatively cheap... awfully convenient with good hours.

[frugaliknowit]

I don't know where you are flying in from, but have you checked Midway Airport?

If you decide to rent downtown, make sure the car rental place is close to the "blue line" if coming in from O'hare or the "Orange Line" if coming in from Midway to minimize the hassles of pickup/return.

[mjb]

I frequenly rent from an Enterprise near the Western Blue Line Stop (on Milwaukee Ave), and an Avis/Budget near the Logan Square Blue Line stop (on Fullerton Ave). (I live about 2 blocks from the Avis/Budget.)

It's not nearly as as convenient as an airport location but the prices are generally good. Check the office hours before you make plans, though.

[chicagomeg]

Can you fly to Lexington, Louisville, or Cincinnati instead of the small town? None of those are likely to be a propeller plane from Chicago.

Check Southwest, they don't tend to penalize you for weird flights like the others do.

Otherwise, I have no great advice on the rental car, but my guess is its about as much of a crap shoot as flight prices. I sort of doubt O'Hare is more because they have such high volume.

[mjb]

Otherwise, I have no great advice on the rental car, but my guess is its about as much of a crap shoot as flight prices. I sort of doubt O'Hare is more because they have such high volume.

The daily rates from airports are usually good but the additional airport-related taxes are usually exorbitant.

[ash7962]

Chicagoan here, you are correct in thinking that rental car rates are higher at the airport, lowest in the burbs.  You can find decent prices in the city itself though, and I think the suburb rental car locations generally have the really good deals on weekend only rentals.  You'll have to do the research yourself, but for something like a 5 day rental it might not be a ton cheaper to go out to the burbs vs the city.  As far as city rental places go, when the SO and I do driving trips we generally try to rent from a place called Budget since they seem to have some pretty good rates.  I'd recommend getting the reservation about a week in advance.   Depending on when you're planning on leaving Chicago, driving out of the city can be a pain in the ass too so keep that in mind.  On the other hand, public transport to either airport is super easy.  I've never flown out of Midway but the blue line's last stop is inside O'hare airport which is pretty damn convenient. 

So, you've got a few options.  1. Rent the car from the city and drive to KY.  I'd see if the fee is the same no matter where you leave it.  If there's an airport you're comfortable with that's closer to KY than O'hare, then I would just pay the fee and return the car wherever is closest.  Saves on driving time and gas since most places require you to return a car with a full tank or pay a fill up fee.
2. Look at planes.  O'hare has daily flights to certain other cities.  All you need is the flight number and you can google how big the plane is to see if you'd be comfortable with it.  You could probably even look at the flights leaving tomorrow to your destination and chances are you'd be on a very similar plane.
3.  Train?  This would probably be the longest travel time, but worth looking into if you don't like planes or don't want to deal with the hassle of returning a car.  Also you can do things on the train that you wouldn't be able to do while driving, and Amtrak is pretty convenient since they're located in Union Station which is in the Loop.  Might even be cheaper than renting a car or getting a plane ticket.

[Argyle]

Driving from Chicago to Kentucky will take around 9 hours, assuming you're going to Louisville — are you sure you want to spend an entire day of your week on what will be a very boring drive?  I'd fly into Louisville.  It's easy enough to find out what kind of plane you'd be on, and many of them are perfectly decent-sized planes.   Or fly into Nashville and drive up — also good-sized planes.  But the drive from Chicago to Kentucky is dreary.

[chicagomeg]

3.  Train?  This would probably be the longest travel time, but worth looking into if you don't like planes or don't want to deal with the hassle of returning a car.  Also you can do things on the train that you wouldn't be able to do while driving, and Amtrak is pretty convenient since they're located in Union Station which is in the Loop.  Might even be cheaper than renting a car or getting a plane ticket.

You could also look at taking the Mega bus. I know it goes to Cincy, Memphis, and Nashville, it may also go to cities in KY.

[dodojojo]

As always, I can count on some good tips from MMM.  I have many complications because I'm arranging to meet a parent flying in from another location so if we're doing mult-city tickets--I have to line up intineraries as much as possible.  The parent is not an English speaker and doesn't drive.  I have to arrange his travel schedule so a friend can drive him to and from the home airport and avoid layovers.

Mlipps, thanks for the Megabus tip.  It doesn't go to the KY city but St Louis is a MB route and the KY city is less than 3 hours away.  It may work if we base ourselves in St. Louis and make KY a day trip.  We have never been to St. Louis so we can use the time to squeeze in an Archway visit.

[Capsu78]

I would be sure to check the distances you are thinking about covering..KY isn't exactly close to Chicago and if you mistime traffic here or Indy you could be in for longish drives in both directions.

[Gerard]

The subway to the airport in Chicago is convenient enough that I wouldn't want to pay the extra bucks to drop off at the airport on the way back.

If you can make it work, have you considered a "triangle trip"? Fly from home to Chicago, fly/bus/train from Chicago to Kentucky, fly from Kentucky home? Depending on where home is, it could save you money and time.

[dodojojo]

I had to hold off on booking the trip due to potential medical issue--but finally got around to booking the flights today.  Switched things up a bit and will be flying to St. Louis and making a day trip to KY.  Then taking the bus up to Chicago and flying out of ORD.  So I've minimized the driving to one day.

The only issue is after factoring in multiple restrictions, I thought I had gotten good value for the airline tickets.  The problem now is that the days we're in Chicago--the hotels are mad overpriced.  There must be some big event/conference(s) during that period as adjusting for a couple days prior gave me much better prices.  Oops.  Oh well, I'll be checking frequently and hope a deal pops up.  I booked a standby with my corporate rate as security.  It's not really my prime choice for personal travel but I wanted to lock into the rate while I can.

[Sibley]

Also look at hotels that aren't right downtown but are near transit. If you have a 10 minute ride on one of the trains, that's not a big deal, but could significantly decrease hotel costs.

[dodojojo]

Also look at hotels that aren't right downtown but are near transit. If you have a 10 minute ride on one of the trains, that's not a big deal, but could significantly decrease hotel costs.

It's just an insane week--on Kayak restricting it to 10 miles from city center and under $220, all I get are a couple of motels, Mid-way hotels and youth hostels.  The city Hampton Inn is quoting $479!

Calling on all Chicagoans....now that transportation has been taken care, let me pick your brains on hotels.  Price being equal, would you go with:

The Drake at 140 E Walton Pl, Chicago, IL 60611

OR

Hotel Allegro at 171 W Randolph St, Chicago, IL 60601?

The Allegro offers free wifi and is more transportation-friendly as we will be coming from Union Station and leaving for O'Hare.  My worry is that the TripAdvisor reviews note the area is kind of quiet at night and I worry about being able to walk about safely.  And though we definitely are not party animals, we would like to go out at night--take public transportation, be tourists and people-watch.

The Drake seems to be a better location in terms of walking about and night life.  But more of hassle traveling from and to Union Station and ORD.  The hotel also only offers free wifi in lobby areas and not in the room.

What say you?

EDIT to say that there's a new contender!  I was able to book the Comfort Suites at 320 Michigan for $50 less than either the Drake or the Allegro.  CS isn't quite the 4 star hotel the two hotels are--but I am a fan of CS/Hampton Inn type places.  Free WIFI/hot breakfast at a decent price.  So throw CS into the mix as you offer your insights!  TripAdvisor reviews seem pretty good and the location looks great.

[Sibley]

I wouldn't be worried about Allegro's location. Yes, quiet, but not in a bad way IMO (single, young female speaking).

[midweststache]

Also look at hotels that aren't right downtown but are near transit. If you have a 10 minute ride on one of the trains, that's not a big deal, but could significantly decrease hotel costs.

It's just an insane week--on Kayak restricting it to 10 miles from city center and under $220, all I get are a couple of motels, Mid-way hotels and youth hostels.  The city Hampton Inn is quoting $479!

Calling on all Chicagoans....now that transportation has been taken care, let me pick your brains on hotels.  Price being equal, would you go with:

The Drake at 140 E Walton Pl, Chicago, IL 60611

OR

Hotel Allegro at 171 W Randolph St, Chicago, IL 60601?

The Allegro offers free wifi and is more transportation-friendly as we will be coming from Union Station and leaving for O'Hare.  My worry is that the TripAdvisor reviews note the area is kind of quiet at night and I worry about being able to walk about safely.  And though we definitely are not party animals, we would like to go out at night--take public transportation, be tourists and people-watch.

The Drake seems to be a better location in terms of walking about and night life.  But more of hassle traveling from and to Union Station and ORD.  The hotel also only offers free wifi in lobby areas and not in the room.

What say you?

EDIT to say that there's a new contender!  I was able to book the Comfort Suites at 320 Michigan for $50 less than either the Drake or the Allegro.  CS isn't quite the 4 star hotel the two hotels are--but I am a fan of CS/Hampton Inn type places.  Free WIFI/hot breakfast at a decent price.  So throw CS into the mix as you offer your insights!  TripAdvisor reviews seem pretty good and the location looks great.

320 S Michigan? If it's the building I'm thinking of, they have a kitchen you can use to make meals (recoup some of your cost). It's not the fanciness of the Drake, but depending on how much time you'll be spending at the hotel, maybe that's not a priority? My family has stayed there while visiting and really liked it. However, it is NOT a four star hotel, like the Drake or Allegro.

Just to clarify--you're only booking a car for one day, and you won't be driving it in the city, correct? Because if you're staying downtown, parking will run you $50/night through your hotels, $30/night if you're lucky and can find a lot not affiliated...

[dodojojo]

I arranged my flights so that I'm driving from St. Louis to KY.  I will not be driving at all in Chicago and will be car-free, thank god.

Yes, the Comfort Suites has kitchens  and dryers/washers.  It used to be an apartment building.  All this is from TripAdvisor.

[dodojojo]

I wouldn't be worried about Allegro's location. Yes, quiet, but not in a bad way IMO (single, young female speaking).

Thank you, that's good to know.  I'll keep checking for deals but CS looks to be the leader for now.  Best price, location and valued amenities (breakfast, kitchen, wifi).  But I'm traveling with a parent--and I kind of want to splurge just a bit and staying at a semi-fancy hotel would be a treat. CS is perfectly suitable--but if there is strong advice for Allegro or the Drake, I would seriously consider them.  With the Drake, I got a good corporate rate but from the description--it's a small room with limited view, etc.  So I wonder if there is a point to such a deal if we're meant to enjoy the perks of staying at the Drake.

[SurlyTroll]

Both the Hotel Allegro and The Drake will be very nice hotels. Both are are in safe area of the city. The Allegro is much closer to the Art Institute, Millennium Park, and the theater district. The Drake is much closer to Michigan Avenue shopping and the Museum of Contemporary Art. Both have easy access to good restaurants. Travel time to O'Hare will likely be 25 minutes faster by train from the Allegro. I love Chicago and missed it greatly since my relocation to Detroit.

[chicagomeg]

I don't know where you live now, but if you're a city person that doesn't mind walking, the loop is really not a big place. I can walk from the river to Millennium Park and back on my lunch break. I'd imagine people who think any of the hotels you mention are too far from things are from small towns where they aren't used to walking.

Also, assuming you have a smart phone, Google maps does a great job with CTA directions so it's ridiculously easy to get where you are going. 

[dodojojo]

Mlipps, I'm a walker/public transportation devotee--no car and live in an area with 90+ walk score. Walking shouldn't be a problem for me.  My travel companion though has some aches and pains so that may limit us a little bit.  The three hotel locations look to be equally good in terms of walkability.  I'm leaning towards Comfort Suites for value.  Second on the list is Allegro--mainly because it's more convenient in terms of public transportation for the Megabus/ORD connection.  And Sibley and Surley Troll have confirmed the Allegro location is quite safe.