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.

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 Hotels.com.

Hi dfrostnh! If you give us some more information, we'll be glad to try and help you.

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? http://metrarail.com/content/metra/en/home/maps_schedules/metra_system_map.html
The other option is to come into the city on Amtrak.

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?

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.

http://www.transitchicago.com/blueline/

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.

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.

http://www.signatureroom.com/Signature-Lounge/

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 www.chicagobestparking.com or www.spothero.com for good parking options.

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.

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 www.biddingfortravel.com and www.betterbidding.com for more information.

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.

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.

Personally, if it were me, once I parked I'd leave the car sitting until I left. (walk and take public transport).

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?

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.

http://www.fodors.com/community/united-states/chicago-odd-or-unusual-attractions.cfm

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.

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.

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: http://www.luriegarden.org/ 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!

dfrost: For an unconventional look at touring Chicago, check out this link.
http://go-go-go.org/2013/02/04/how-to-visit-chicago-like-a-chicagoan/
(Warning: Adults only. Language and humor herein may be found offensive by some persons)

Toucan !!!! thanks. The boat tour is on our maybe list. Bitter thanks for the link to the other thread. I'll check out Lurie Gardens and do I dare look at Dave_Ohio's link? I think the L to the closest station and then a cab might be the best idea. My friend says she'll be fine with her GPS but if I take the earliest flight, I'll be arriving during commuting hours and expect the traffic will be awful. If I weren't dragging a big suitcase and heavy carryon, a 6 block walk would be fine.
My friend thinks she would like the City Greeter Chinatown tour.

Hi, dfrostnh.

I think your hotel package is a great bargain. The hotel feels about 1 block off the tourist loops, but a good location, so don't worry about that. Definitely, have friend go on her own to the hotel to park on her own, and you can take the blue line train (the only train) from O'Hare to the city.

However, if you're feeling fatigued and the bags are really heavy, (intent on a taxi anyway), I'd recommend getting off the blue line train at Clark/Lake, go up to street level and catch a cab from there to Lasalle X Ohio. Always difficult to get your bearings upon getting up to street level, but if you can get yourself over to Lasalle, that would be slightly better than Dearborn. (You may as well do this plan, because you'll not save that much money if you transfer from blue line @ Jackson Station to the Red line train, ride it north to Grand, take a cab from a much more congested area.)

Then, you and your friend can arrange to meet someplace nice. The area immediately surrounding your hotel doesn't offer nice meet-up places. But don't let it concern you. You'll be here in a better weather month, so a 1-2 block walk will get you lots of nice options. A recco is the Starbucks straight east on Ohio (from your hotel) to State Street.

RE: Art Institute Day
Great idea, and great price to get in. Taking the bridge to Lurie Garden (lovely) as suggested is a great idea. You can do this and (heading north through park) see all of Millennium Park, which is wonderful. The Chicago Cultural Center is across the street and worth popping in to explore and see the Tiffany designed dome.

Lunch is available in the museum, but if you’re looking for lunch or dinner reccos, let us know and we can weigh in.

RE: Chinatown Tour
Ew... I admit, I've not taken the tour but have been to our Chinatown several times. I find it horribly, horribly dreary... and being Asian myself, I feel somewhat bad deterring anyone from patronizing the business there. With so little time, pass on Chinatown.

RE: Art galleries
Your hotel isn't far from the (somewhat smallish, concentrated) gallery area of Chicago. It's centered around Superior X Wells/Franklin. Nice, quiet area... if you go there, walk north on Wells street (Lasalle Street is just ugly), to Superior. But do a search for galleries that tempt you beforehand. There may not be enough, though there is a Luminaire modern furniture showroom at 301 W Superior that I enjoy drooling in.

If you want restaurant reccos for b’fast/lunch/dinner, evening ideas (theater? Improve? Jazz? Fine dining?), let us know what your tastes are.

If weather is nice, a walk north on Michigan Ave to Oak, then taking the underpass to Oak Street Beach is a nice thing to do, as the view can be very pretty.

Have fun!

Re arriving during commute hours - a favorite memory of ours is taking the L from O'Hare and watched the standing still traffic ( on the Dan Ryan Expressway?). We were so happy to be on a train!

on the Dan Ryan Expressway?

no biggie, but it's Kennedy Expressway...

that is if you arrived at O'Hare

We went to Chicago last May and had a wonderful time. Weather was spectacular. Loved, loved, loved the architecture boat tour. The greeter program has an architecture tour, too.

Did not have a car and did not need one, but I admit one Saturday night it got a little scary on the streets downtown.

AA, that's why I put the question mark!

Yeah!! You're coming to Chicago!! I'm excited for you. Have you ever been before??

I looked into that same hotel over Christmas when we were going to do a family thing for the Christmas parade. It didn't work out at the time but I thought the hotel looked great and it is in a good location. The prices were very good.

Chicago is expensive, but there is lots to see just walking around. You are going to love the Art Institute!! I lose track of time in there, it's probably my favorite place in Chicago. And I also have to recommend the Tiffany Dome at the Chicago Cultural Center. It is free and right across the street from Millennium Park and of course the Bean. Love, love Mellennium Park too and the splendid gardens. And if you smell some good popcorn as you are strolling down Michigan Avenue you have found Garretts, very famous in this area.

The architecture boat tour while pricey is very, very worth it. I have lived in the Chicago area my whole life and only did the tour two years ago. I second the part about Chinatown. With limited time, it's kind of iffy. But I think the idea about drinks at the John Hancock lounge (96th floor) is a great idea.

I wish you had more time in Chicago or I would suggest a GTG, it would be so great to meet you.

I grew up in Chinatown. I recommend it for the food and some of the kitschy shops. You can take a water taxi for $8-$10 R/T from Michigan Ave. to Ping Tom Park in Chinatown and walk over to the restaurants and shops.

Chgogrl and others, thanks for the directions. It looks like it will be very simple to add the Tiffany Dome and Lurie Garden to our Art Institute visit. Even with a guidebook, it's hard to figure out what's do-able in our limited time. Your advice is a big help. I usually like to get out on the water for a different view of things so the boat tour sounds good. Funny, I did check out the "adult-content" review and the recommended cheap hotel but the cheap hotel is much more expensive than the BW.

I'm disappointed by the Chinatown discouragement. I've been to Boston's Chinatown (great food tour there) so maybe the negatives are similar. My friend likes to try Chinese recipes but has never visited a Chinatown so I think we will take Dave-Ohio's recommendation and give it a try. Dave - can you recommend a good bakery there?

barbrn, since I live in a rural area, rarely visiting Boston because DH hates cities, this is going to be great fun (leaving DH at home). We are arriving early to visit Chicago before heading to a conference in St Charles.