Chicago Challenge

Old Feb 25th, 2013, 09:56 AM
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Chicago Challenge

A friend and I have one or two days to explore Chicago before we attend a conference in May. She is driving. I am flying but haven't chosen an airport yet. She is willing to pick me up at the airport. Any tips on making airport pickup easier for her? Do any of the hotels have free shuttle pickup? Any tips on getting a good deal on a hotel with hotwire or priceline that might have free airport pickup to spare her the job of driving into the airport?

The only definite plan we have is to visit the art museum. I have the Fodor's Chicago guide but I need suggestions about where to stay. We need a budget hotel. Since she has a car we can drive in and out of the city but perhaps it's like Boston and we'd be better off staying in the downtown area near public transportation.

What's your favorite Chicago neighborhood to explore? We like a variety of food, art galleries and unusual shops.

Your Chicago advice is appreciated!
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Old Feb 25th, 2013, 10:08 AM
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There are no hotel shuttles to downtown hotels.

Where is she coming from? If she's coming from the south, picking you up at O'Hare would be a nightmare. Likewise, if she's coming from the north, picking you up at Midway wouldn't be so easy. You can get from either major airport (O'Hare or Midway) to downtown via public transportation (the "L") very easily.
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Old Feb 25th, 2013, 12:46 PM
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You mention a budget hotel and also parking which is expensive in the city. Cheapest is the underground parking at Millenium Park. You can take a blue train downtown from O'Hare or the Ornage Line from Midway unless your friend is driving past those locations.
Hotel prices vary according to the time of year and whether there is a large trade show going on. You may get a good deal with Hotwire or
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Old Feb 25th, 2013, 06:06 PM
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Hi dfrostnh! If you give us some more information, we'll be glad to try and help you.
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Old Feb 25th, 2013, 09:37 PM
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There is no advantage to having a car to park in Chicago.
Can your friend find a cheap or free place to park near a Metra station?
The other option is to come into the city on Amtrak.
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Old Feb 26th, 2013, 03:18 AM
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OK, here's an example. I found a decent price at Best Western River North for the Art Lovers pkg which includes 2 tickets to the art institute @ $23.00 for a total value of $46. They have free parking which would save u the $30 pkg fee at Millenium Garage. The garage is $14 for an early bird special (get there before 9am) but the Art Institute doesn't open until 10:30.

The hotel is right near a CTA bus stop which would be a cheap way for me to get from O'Hare to the hotel, sparing my friend a drive into the airport. The ride is about an hour but it sounds like finding the bus station at the airport is an adventure.
Question: I'll be dragging a suitcase and one carry on - is this really feasible to take the bus? I'm used to Boston's Logan express transporation that puts baggage under the bus. Is this what they do on the CTA buses?

If my friend picks me up at O'Hare, I would think the best thing for her to do would be wait in the cheapest airport parking lot? Which is that? Is there a special parking lot of people/cars waiting to pick up?

My friend is driving in from Buffalo so I guess she would be coming in from the south?
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Old Feb 26th, 2013, 05:00 AM
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The Blue line train station is right at the airport. No need to take the bus. As long as you are willing to deal with the luggage you will be fine. The train starts/ends at the airport, so you should be able to find a seat and enough room for the luggage. It takes ~45 minutes to get to downtown area. Perhaps she can pick you up at whatever station is nearest to the hotel.
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Old Feb 26th, 2013, 05:13 AM
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Looking at the map I would suggest that she meets you at the Grand Ave station which is only few city blocks from the hotel.

The station is located at intersection of Grand Ave/Halsted St and Milwaukee Ave.
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Old Feb 26th, 2013, 05:29 AM
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and one more suggestion,

on a clear day or evening visit the John Hancock building, BUT instead of going up to the observatory and paying ~$15 each to get up there, visit the Signature Lounge at the 96th, which is only one floor below, the elevator ride is free, you can have a drink and enjoy the same gorgeous views of the city.
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Old Feb 26th, 2013, 07:29 AM
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As an earlier post says, the CTA Rail station is in the airport. Follow the signs from the baggage level of any domestic terminal that say "CTA Trains to City." A one-way ride from the airport is $5. Purchase a farecard from the vending machine at the station. If you'll be taking more than 4-5 rides on public transit within a day, you can purchase a one-day pass that allows unlimited rides for a 24-hour period. They cost $10 and are available at the currency exchange on the lower level of the Hilton, adjacent to the rail station.

If your friend is coming from Buffalo, she'll be entering the city via the Dan Ryan and Kennedy Expressways (I-90/94). If she really wants to pick you up, you can take the Blue Line to Western Avenue. The station has elevators and escalators. There's a McDonald's about a block north at 1951 N Western Ave. She could wait there and grab a coffee or ice cream.

As an alternative, you could take the Blue Line to Clark/Lake (which also has elevators), then catch a cab for under $10 and meet at the hotel.

The CTA site has a trip planner, you can plug-in your starting point and destination and get possible routings. It also tells how to track buses and trains with a smart phone.

Finally, don't blindly assume that a hotel with free parking is automatically your best value. Depending on when you're visiting, you may be able to find a great rate on a room at a 3-4 star hotel on the bidding sites, then find inexpensive parking nearby. Check or for good parking options.
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Old Feb 26th, 2013, 10:39 AM
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As an addendum to what AAFF suggested, try to go to the Signature Lounge in the Hancock Building around sunset. I went at night and thought the lights of Chicago were beautiful......but Lake Michigan was a huge, black void. If you go just before sunset, you'll be able to see the city, the lake, and then the lights.
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Old Feb 26th, 2013, 11:37 AM
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Your friend does not need to pick you up at the airport. As mentioned before, it is easy to take the train into town. In fact she would probably be better off not even driving to Chicago. She could take Megabus from Cleveland (there may even be a Megabus available closer). If driving, she will have $40 each way in tolls, gas and she will have to pay to park. If she is driving alone, Megabus is much cheaper--in fact, my last trip, I only paid $7.50 RT Cleveland to Chicago. A car is a pain in Chicago.

Chicago can be very nice in May--good idea coming a couple days early. You will enjoy the city.

You definitely need to try Priceline and Hotwire for hotels in Chicago. Stay in the Loop or Magnificent Mile. Unless there are some major conventions in town, you can get a good rate on a hotel in town. See and for more information.
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Old Feb 26th, 2013, 12:47 PM
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But don't use Priceline unless you're prepared to share a bed! On Hotwire, you can put in "3 people" in which case you're sure to get a room with 2 beds.
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Old Feb 26th, 2013, 01:51 PM
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We're making progress. We booked Best Western River North which has free parking. We can always cancel but thought we better get something now that looked decent for Chicago prices. Unfortunately, friend is driving because she has lots of things to bring. I can get an early flight. If I fly into Midway I can travel home with another friend.

I should be able to navigate bus and L. Next question: would it be better for me to take the L and then a cab to the hotel (1/2 mile, I think) or ask my friend to pick me up at one of the stations that has a parking lot? Would she be better off having me help navigate to the hotel or would it be just as bad try to get to one of the Orange Line stations that has parking (I'm guessing they are close to the airport).

I very much appreciate help with these details.
dfrostnh is online now  
Old Feb 27th, 2013, 06:28 AM
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Personally, if it were me, once I parked I'd leave the car sitting until I left. (walk and take public transport).
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Old Feb 28th, 2013, 02:30 AM
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Bitter, that's the plan once she picks me up and we get to the hotel. Hotel says we can park the car on day of arrival even though room might not be ready until 3. We can also leave it in the hotel parking lot until 5pm on day we check out. I haven't been to Chicago in probably 10 years but used public transportation to get around.

Since we have very limited time, in addition to a drink at the top of John Hancock and probably several hours at the Art Institute, I think we should try a Chicago Greeters tour. Any recommendations?
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Old Feb 28th, 2013, 06:18 AM
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dfrostnh: I think if you search for chicago you'll find lots of good threads. Here's one I started and have added to over a couple years. Admittedly, it was for new, less traveled ideas.
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Old Feb 28th, 2013, 07:30 AM
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I think just meeting up at the hotel might be easier than coordinating a pick-up plan. From O'hare you could take the blue line to Jackson, transfer to the red line (free transfer, follow signs to red trains through corridor, board Howard-bound) get off at Grand/State and walk the four blocks to the hotel.
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Old Feb 28th, 2013, 07:52 AM
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When looking at Blue line stations, you want one with elevator ,look for handicapped insignia. I always get off at Clark/Lake and walk or take a taxi to hotel.
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Old Mar 1st, 2013, 07:09 PM
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I would agree with blue star. See citylights post above that gave you the station to make your destination from the airport, then take a cab from there. It would really be much easier on your friend.

There are so many great things to see in Chicago. I see you have been there before, have you already done the Chicago Architecture boat tour? It's one of my favorite things, such a different perspective of the city.

I mentioned the Lurie Gardens in Millenium Park on the other thread. Here is a link to it: I think you might really enjoy it.

I know you have limited time. You might find you get seduced by the Art Institute and not have much time for more!
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