Hi Joanne,

Like others have said, if you are staying in the city you definitely do not need a car, our public transportation system can get you anywhere you need to go in the city. If this is your first time in Chicago I would stay in the River North neighborhood, it's a great location central to a lot of great things the city has to offer. Great hotel options are Thompson Chicago, Acme Hotel Company Chicago, and The James Chicago Hotel.

I don't think a car is necessary unless you're leaving the city, you can pretty much get around by walking or using public transportation. I would look into one of the Kimpton hotels in town-they are all located pretty centrally and the amenities as well as service are unparalleled for what you pay for. Hotel Monaco, Hotel Palomar Chicago, Hotel Allegro Chicago are the three in town. Have fun!

Agreeing with what others have said, I'd recommend against having a car. As is the trend in other cities that privatize parking, Chicago runs meters 7 days a week until 10pm in most neighborhoods, and parking can be as high as $6.50/hour in the loop and $2/hr in most other 'hoods. http://chicagometers.com/cost--hours.aspx

I'd absolutely suggest Chicago's extensive train and bus system which will cost you $2.25-$2.50/ride, or, if you prefer the more direct route, Chicago taxis are pretty reasonable, readily available, and will take you a couple neighborhoods away for $10 on average. Not trying to promote other businesses here, but Lyft and Uber have extensive operations in Chicago as well and their apps are super convenient.

With that said, for 2 days of visiting, anything you'll have time to see is most definitely within a 3-5 mile radius and very walk-able in the summer.

Now to add to the conversation, there are a ton of car rental locations in the heart of Chicago's business district, the Loop. I'd recommend doing a one way rental from Iowa to one of these city locations. They will all be in a parking garage where you'll hand off the car to an attendant who will usually look over the car and give you a receipt that you take to the office to close your contract.

Once you are ready to leave town, the trains will take you direct from downtown to either O'Hare or Midway airports in less than an hour.

There are plenty of options outside of a car rental that will allow you to get to where you need to go without having to worry about parking, tickets, or towing. You can use the city train called the EL (elevated train), you can use taxis, uber, lyft, sidecar, the buses. All these options will get you where you need to go with little effort. If you need to get out of town into the suburbs, then you might need a car rental, but, if its just two nights and in the city, time will fly by and you will be just fine without it. Many people living in the city try to get rid of their own cars unless they use them to get beyond the city. 

Hi Joanne! 

Unless you plan to head to the suburbs of Chicago for anything, I say ditch the car. Chicago's CTA is really great, and it's super easy and affordable to get around. Having a car is usually more of a burden in Chicago and parking isn't cheap either. Chicago also recently put in Diivy bikes that you can rent all over the city which could be a fun way to explore as well.

As for hotels, I'd stay in River North as it's a great central location. My top affordable picks would be Hotel Palomar Chicago or The Westin Michigan Avenue Chicago. Have fun!

If staying in downtown Chicago, I wouldn't recommend keeping the car unless you really need it. Parking is expensive, traffic is...intense..., and GPS devices have trouble knowing where you are. Hotels? Depends on what you're looking for. I enjoyed the Dana Hotel and Spa, Renaissance Blackstone Chicago Hotel,The Palmer House, and Drake Hotel depending on the style of hotel you are looking for (and location).

If you are staying downtown a car is just an expense.  You can walk to most everything or take a cab or public transportation.  Part of the fun in Chicago is walking to destinations.

You honestly don't even need to rent a car, just download the Uber app onto your phone and you will be fine. Also, you might want to buy a Ventra card at a Walgreen's or at any L station when you get here. I live less than a mile from Wrigley and I don't own a car and have not needed one except to go to the suburbs to visit family. 

Depends on if you like expensive tickets and parking? Find out the price of hotel parking. Find out about Red Line and El Train. Cabs are cheaper than tickets.

Parking is a hassle in Chicago Unless you pay for parking which can be expensive. It's better to take public transportation or UberX. hassle free. However, if you don't mind walking few blocks or even paying 5/10 dollars for a space for few hours then I say keep the rental car

No car needed once you get there! I'm from Iowa and travel to CHI frequently. Any hotel in the River North area is great. Hotel Felix Chicago is perfect.

No. Lots of buses. Omni Chicago Hotel, all suite hotel, on Michigan Ave.