We are flying into Midway airport renting a car and taking a road trip before coming back to the Chicago area. When we return we will be staying at The River Hotel in Chicago for three nights. Any reviews of this hotel? I am wondering if when we return we should just drop our rental to Midway and take a taxi to the Hotel? The airport looks to be 45 mile drive from the Hotel. How crazy is it to drive in Chicago? Any idea of how much a taxi would be? We are from OK so mass transportation is extremely unfamiliar and kind of a scary thought with luggage.

Drop car off at Midway and take the Orange line(train) into the city. Get off at Clark/Lake station which jas escalators.. Walk a few blocks to hotel. Very easy and inexpensive.

And in answer to "how crazy is it to drive in Chicago", the answer is "pretty crazy". We're familiar with public transportation, so not as concerned about it as you are (from lack of experience), but we have been on the "El" coming from O'Hare and we could see the standstill traffic below us on the expressway. Couple that with the fact that you do not need or want a car IN Chicago, and I agree with HappyTrvlr. How much luggage will you have (my answer might differ if you have more than one carryon size bag each).

Midway is no where near 45 miles from The Loop, more like 10. Yes, you should drop your car and take transit, parking at most downtown hotels is around $40-$50 per day.

A taxi would likely be around $25 outside rush hour. If you sit in traffic, the meter will keep ticking.

After you drop your car, follow the signs through the terminal that say "CTA Trains to City". You'll need to purchase a Ventra card and load value onto it. You can do the math to see if it would be easier to pay-per-use or select an all-day pass. Single trips are $2.25 and a 1-day pass is $10.

The card is $5 which you can get refunded if you register it. Check www.transitchicago.com for fare info, maps, a trip planner and how to track trains and buses with a smart phone.

Take the Orange Line to Clark/Lake. The station has elevators/escalators. You can hop in a cab for a few dollars, but if the weather is nice, it's a pleasant 8-10 minute walk. Walk one block north on Clark to Wacker Drive and turn right. Your hotel is about five more blocks. The State/Lake stop is a couple blocks closer, but you'd have to schlep bags down the stairs.

To avoid the stairs at State/Lake, you can transfer at Roosevelt to the Red Line toward Howard. Then exit at State/Lake. (The subway has escalators to street level, the L doesn't.)

Your hotel is well-located and most sights are within a short walk. Buses and trains run frequently and are easy to understand. If you're confused at a rail station, ask the agent.

You may be from Okie but it is time to learn how a lot of the world gets around. You could drive and park in Chicago ok. Just slow and expensive and sometimes crazy. There are many who might ask, WHY ??? when public transit is so easy. The orange line is full of people with luggage. Why? because it is coming from the airport and most people have luggage. If you don't want to walk to your hotel, grab a cab when you get off the "L". Cabs are everywhere. Just raise you hand and wave. Don't bother with the transfer to the Red line. Just adds a wrinkle that is not needed. You will get confused and turn around so just use your goggle maps on your smart phone. The L is very safe and convenient.

The River Hotel is the best. Not a huge elaborate lobby or a lot of extras but IMHO it is wonderful. I have stayed there 3 times. The rooms are a little small but for sleeping and cleaning up they are great. Very clean. The sheets feel like grandma ironed them for you. The staff is wonderful. It is half a block from Michigan Ave. I found it very centrally located and easy to get anywhere. The staff is more than willing to help you find the transportation that you need.

I agree with everyone about turning your car in before settling into the city. If you are traveling light, I have taken the Orange line to the State/Lake stop and used the stairs. The Orange line starts at Midway so it is pretty empty at that point and I have never had an issue with luggage.

After my last cab ride out of Chicago, I will never take a cab to or from the airport again.

Thank you for the advice. I wish we were traveling light but I fear we will have more luggage than we can easily handle on the train. This was my fear from the beginning. fmpden I promise, we (as Okies) are well traveled and very aware of mass transit. The luggage is and always was my concern. I still have nightmares from the time we got off a three week cruise in Amsterdam and lugged luggage around trying to get on a train. Thanks for all the help, we will take a look at our luggage and decide if it will be the Orange line or taxi.

With a lot of luggage (more than a medium size roller bag and purse/backpack), I'd hop in a taxi--which from Midway could be closer to $35-40 (if traffic is thick; $25-$30 if traffic is flowing.) It is expensive, but much less stressful than driving and paying a $50/night parking fee at a city parking lot.

If you can do an escalator/elevator with your luggage, and not exhausted from driving, the elevated train is really very easy. But sometimes, just committing to a taxi and the expense is just so much nicer.

Your hotel is in a great location, so well done there.

Have a great time in Chicago.

I'd take a taxi (or Uber) if I had a lot of (or particularly large or unwieldy) luggage.

Is there a reason you are taking a boat load of luggage?

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Skipping over the condescension toward the Okies who are evidently presumed to be grass-chewing inbreds by the urban snobs on the board, the fact is Midway is not 45 miles from central Chicago (or really anyplace in Chicago) and I'd strongly consider dropping the car upon return to Chicago (which is congested generally, and will have you dealing with driving under the L once you're in or near the Loop).

Give this a try for your taxi fare: http://www.taxifarefinder.com/main.php?city=Chicago

I can say definitively that a round-trip taxi from Midway to your hotel will not exceed the cost of 3 days car rental and parking, so it seems an easy choice to me. If you think you can manage the El, then do that, but if you can't, just take a cab.

Now, now, folks...Can't we all just get along?

I think that this reply: "You may be from Okie but it is time to learn how a lot of the world gets around."

Was in direct response to this comment by the OP:
"We are from OK so mass transportation is extremely unfamiliar and kind of a scary thought with luggage."

Although I would not have said the first in quite the same manner, IMHO, when you go to a destination, you have to learn to operate in the same manner as the local population does. And, in a major metropolitan area such as Chicago, NYC, etc., that means using public transportation and to **forget about the using a car**.

Fortunately, the CTA in Chicago is extremely easy to use and cost-effective. Just take a look at their website, familiarize yourself with it - and look at the online maps sections. A picture is worth a thousand words. You'll see where all the bus routes travel, as well as the 'L lines, and how they can be utilized to get to the various attractions.

***Particularly note that the River Hotel is immediate to all of the 'L lines and State Street, south of the Chicago River, is a major artery for the various bus lines.*** Also please note that it is much more likely that you would be using busses, rather than 'L lines, to get to the immediate attractions, especially if they are near the lakefront. As a rule of thumb, the 'L lines are utilized to go longer distances - such as to/from the airports, into the outlying neighborhoods and so forth - and the busses are utilized for the majority of the transportation - travel within those or near neighborhoods and areas, near the lakefront area, etc.

@OP: It would be greatly to your benefit to substantially edit the amount of luggage you are bringing. If not only for the sake of convenience and time savings (waiting on checked luggage at the airport), but with respect to the costs involved as well when you are flying.

There really isn't any reason why you need such a lot of luggage, even if you are taking a road trip beforehand. Just pack interchangeable separates - a little goes a long way.

It's pretty crazy to drive in Chicago, but depending on the time of day, and where your "road trip" is taking you, you might consider swinging by the hotel to drop off your luggage and then taking the car back to Midway. Then you can happily use the transit system until you're ready to head back to the airport. It has been several years since we flew into Midway but it was not hard to get from there to downtown.

If you are driving in to drop luggage look for a car drop site downtown. All of the major car rentals have rental locations in the Loop area. It is crazy to drive in to drop luggage and then drive out to drop the car. That really doesn't make much sense.

The luggage issue doesn't make a lot of sense either. She has gone from "mass transportation is extremely unfamiliar" to "are well traveled and very aware of mass transit." Which is it? Familiar or not. Generally experienced travelers have a good handle on the amount of luggage necessary. Obviously, if you have a several large suitcases that are not easily handled, then it is taxi or Uber.

Two of us have learned slowly but now travel including cruises with three carry on size bags - two backpack style and one rolling. If not on cruise then the rolling bag stays home.

Without knowing where they're coming from, it's impossible to say how far out of the way it would be to go to the hotel first. I agree it is not ideal, but if they will have a lot of luggage, it may not be any more cumbersome than driving to the airport and stuffing all their luggage into a cab after dropping the car off there. But a car drop-off downtown is an excellent idea, and the fee for a separate drop-off might be offset by what they don't have to spend on a cab.

Very interesting to read comments about oneself from strangers...
I so appreciate any help I can get when traveling to a new place.
Let me clarify my statement "mass transportation is extremely unfamiliar" Perhaps I initially misspoke. While we are familiar with mass transportation when we travel. We live in a state with wide open spaces (love) and no huge masses of humanity (love) so we do not deal with mass transportation on a daily basis. For that reason it make me (perhaps not my husband) anxious when in an unfamiliar location carrying luggage. We will be traveling with two carryons and a rolling garment (necessary for clothing for a wedding we are attending on our road trip) I appreciate the idea of checking for a rental locations closer to downtown. That makes sense.

Perhaps I was sensitive to the comment that Okies need to learn how the world gets around. We, as proud Okies, DO get tired of being treated as backwoods hillbillies with absolutely no sophistication or education about the world we live in....so if I was overly sensitive I do apologize.

Thank you for your help. We look forward to our first visit to Chicago.

Have you looked into the cost of mailing or sending your wedding togs UPS (or another ground service) to the wedding destination? Might save you some $ as well as freeing you up from lugging that rolling garment bag around (as well as paying the airline fees for it.

BTW - JMHO and I'm not climbing up on any soap-box here - but those areas of the country which are "car-centric" need to do some serious thinking about what they will do when a finite source becomes depleted. It may not be within the next few years, but it will eventually happen.

I just wanted to add that I didn't direct that last comment towards the OP in particular. I only mention it because of a previous comment. This isn't an issue of urban dwellers vs. others.

It's just that people who depend solely on their cars need to reconsider what they will do without public transportation when that day comes when they can no longer use them - and, hopefully, invest for the future before it does.

Just my 2 cents.

I was in a similar situation last year - traveling from Northeast to Atlanta for a wedding, then continuing by rental car for a 2 week road trip before flying home from Atlanta.

After much consideration and worry, I sent wedding clothes & shoes via UPS. My sister mailed it all back to me 2 weeks later. Without the garment bag, we were able to take mass transit from airport to hotel and pick up rental car at an off-airport site which was cheaper, even though car was returned to airport.