Here's an idea to save some $$ - particularly if you are coming to the city on a busy summer or fall weekend and the downtown hotels are booked up. In that case, Priceline or Hotwire or any other internets booking service is not going to be much help. In that case - and especially on weekends - great deals can be found in some of the northland Chicago suburbs like Deerfield. These are places with a lot of big businesses and employers, and plenty of quite nice hotels that are relatively empty outside the business week. In summer 2013, I stayed for a weekend at a Hyatt property in Deerfield for a fraction of the price I would have paid in the city - and I took the Metra too and from the city.
From the north side 'burbs like Deerfield, Metra has good reliable service, numerous trains in and out of the city, and convenient arrivals and departures from Union Station. (Deerfield Station has free parking on the weekends - I like that price.) Now, there are times when you really want to stay in town, and the commute in and out on the train is not really worth it. On the other hand, I love feeling that I am saving a few dollars that I can spend on good restaurants and shopping. I recommend Metra as an option.
You shouldn't have a problem with luggage as long as you are not traveling on a morning or afternoon express train. The express trains are usually between 6:00 a.m. to 8:30 a.m. going into the city from the suburbs and 3:30 p.m. to 6:30 p.m. going from the city back to the suburbs. Those trains are jam packed with work commuters and even though you could bring luggage aboard you will probably be looked at kind of funny. There are overhead metal racks to put the small luggage, but you would have to keep the large roller one next to you if you stood up or next to you in an empty seat and I wouldn't advice that with people looking for a seat.
Your other options are to take a local train (one that stops at most or all stations on the way into the city). These trains are far less crowded then the commuter express trains, but it will take you longer to get from University Park into the city. The trains that run between 8:30 a.m. to 3:30 p.m. are usually all local trains. There are some local trains that also run during the commuter times.
Chicago has a rather extensive commuter train system called METRA which comes into the City of Chicago from all parts of the suburban area. The trains come into several downtown locations with the 2 largest debarking points of Union Station and the Ogilvie Transportation Center.
There are a number of different locations in many suburbs to the north, northwest, west, southwest and south that come into the city often several times per hour. Also mainly used by commuters, travelers to the area that come into Chicago can also opt to arrive here each day on the commuter trains. Although some of the trips could be upwards of an hour ride into the city, there are a number of different options which could shorten the trip somewhat.
If you do ride with the commuters in the mornings coming into and the evening going out of the city you can ride express trains which go to specific destinations in as little as 30 minutes. The trains that run outside the general commuter times in the morning of 6:00 a.m. to 8:30 a.m. and 4:00 p.m. to 6:30 p.m. in the evening will more then likely be the trains which stop at most stations along the way.
Do not - drive into Chicago - the worst traffic, and outrageous parking prices (i.e - our hotel - $50.00 a day to park)
Best suggestion - if you are driving from the east, stop at South Bend and visit Notre Dame, then drive to the Airport. The South Bend Airport has an Airport, Bus station and a metro. Park your car (cost us $24 for 3 days) and take the South Shore line (an electric train) into downtown Chicago's Millenium park station - $11.75 each way, 2 hours - no stress. South shore line is accessible at most stops along the way including South Bend and Chicago.
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To get from Kenosha to CHicago, use the METRA. A station in Kenosha is at 53rd and 13ths St. Plenty of free parking across the street or in the ramp a short block away. The Police Station is right there too so it will be safe.
The local stops at 23 stops or so, a lot, takes about 1 hr 40 minutes. Try to catch one that doesn't make a lot of stops. 1-way is $7.50 right now, half for kids 7-11.
* To get to Wrigley field, stop at the Evanston/Davis exit (you pay half of the ride all the way downtown), walk one block east and find the Purple Line/Davis line down to Red Line then to Wrigley Field. Easier than it sounds.
I heard over the speaker you get a $3 surcharge if you use cash instead of a ticket when leaving Chicago, so buy a ticket there. When leaving Chicago, just pay cash on the train.
Big board on the left as you go in says which track to get on.
Station for this line is OGILVEY STATION, a block away from Union Station. You want the Union Pacific North Route (to Kenosha).
The other option is Amtrak from Racine, at about $20 1-way, but with only 2 or 3 stops, faster.
I take the South Shore from South Bend to Chicago all the time. I have also taken the South Shore from South Bend then hopped the Blue Line to Ohare. What you have to be careful of it the time. If you are catching a flight, you have to allow for all the security stuff at the airport. I have many times seen great flight deals out of Chicago, but by the time I put in the cost from South Bend (SB) to Chicago, the deal isn't there anymore. I had an opportunity last year to attend a seminar 1/2 mile from Ohare and realized it would be a perfect time to check out a time line if I was to ever take a flight using mass transit. The class started at 9, and we couldn't get a train that left early enough to get there on time. We ended up driving to Michigan City because they have trains that leave earlier. They also don't charge for parking at Michigan City. I don't have the metra schedule, but I know you will take the blue line to Ohare. From SB you will take the SS to the last stop then walk a couple blocks to hop onto the Blue line. Don't worry about how to get on the blue line. Once you get to the station, anyone will tell you how to get on it. The locals are very good about that. It's a couple hours to get from SB to Chicago, then another hour and a half from Chicago to Ohare on the blue line. I remember thinking that I if I was going to have to catch a flight, I needed to allow 5 hours from SB. Hope this rambling helps!
Metra is a suburban railway system in the Chicagoland area. We were staying in Crystal Lake, about 50 miles outside of Chicago, and used the Metra Union Pacific - Northwestern line to travel to Ogilvie station in Chicago center. The trains departed almost hourly at the weekend.
Using the Metra service was really easy and convenient. The journey took about 1 1/2 hours (there are some faster express trains, but not at the times we travelled), and cost only $5! At the weekends you can get a $5 weekend ticket which is valid for the entire weekend! By car the journey would take at least as long, much longer during busy times.
You can buy your ticket on the train from the conductor, but you will normally pay ~$2 extra for the privilege. If the station you started from doesn't have a ticket desk then this fee is waived.
The trains we used were all double-decker, with 2 rows of souble seats on the lower level and 2 rows of single seats on the upper level. Each carriage had a toilet. The carriages were robust, made from stainless steel, not pretty but clean and functional. The train conductor moved through frequently and we never felt unsafe. During rush hour the trains can get very crowded with commuters. On the back of each seat there is a hook where you can clip your ticket, to save being disturbed by the conductor.
I was impressed by the Metra service, especially by the price. I would recommend this service to anybody travelling in the area, it is cheap and convenient, and usually faster than travelling by car.
I've never seen a need to have a car in Chicago. Its much easier just letting the taxis or the 'El' take you where ever you wish to go. Plus, most hotels charge around $40 per day to park a car. So I'd find an alternate way into the city.
From Indiana, the easiest is the south shore line which runs all the way from South Bend to the middle of Michigan Ave (right in the middle of the 'Mile').
One way for that distance will run you about $10 per person, saving enough money for taxis all over the city.
Union Station is Chicago's main train station and the base of Amtrak and most METRA lines. It's on the near west side of Chicago's Downtown, and is fairly accessible on foot.
It's a large complex, so it can get somewhat confusing. Keep in mind that there is both a north and south concourse and trains leave from both. Boarding generally opens up about 30 minutes before the train's scheduled departure (for METRA). If you get confused, there are lots of helpful security officers who hang out at the doors to the platforms.
If you're coming in, get food and drinks beforehand if necessary. What's available in the station isn't very good.
METRA is a quick and cheap way to get into town. Stations are all over the suburban areas, so no matter where you are in Chicagoland, you're likely within a couple of miles of a station.
The stations 10 miles or so out of Downtown and further have parking areas which are free on weekends and public holidays. If you're staying in the 'burbs, this is absolutely the best way into town.
Tickets should be purchased at the station's ticket window if possible. If closed, they can be purchased from the conductors. However, if the window isn't closed, the conductor will charge $2 extra. The Union Station windows are always open.
If traveling on the weekend, purchase a $5 weekend pass. It'll typically be made up for in a single round-trip, and works on the 3-day weekends (Memorial Day, Labor Day, etc).
Kids love the trains too, and the conductors are very friendly. It's actually a great family experience.
The trains are the same style as CalTrain in the Bay Area, where there are actually two floors with the second much narrower on two sides and overlooking the first.
You can download schedules on their web site, or they're all available at Union Station. Look for the express trains (that skip a stop), and keep in mind that they run on a much more limited schedule on Saturdays and Sundays (which themselves both have different schedules).
You can still walk, take cabs or take the EL if you are around downtown, but the trains go very far into the surrounding suburbs. It's very easy to live affordably in the suburbs and commute downtown.
Metra is Chicago's commuter train. It will take you to the suburbs and even into Wisconsin and Indiana. The Metra Electric station in downtown Chicago is located on Randolph Street (near Michigan Ave). The other Metra terminal stations are located at Chicago's Union Station and the Ogilvie Transportation Center. The cost of a one way ticket depends on through how many zones you travel.
I usually travel from the University of Chicago on the Southside to downtown, that is from Zone B to Zone A (through one zone) and the cost is around $2.
A very convenient way to get downtown from O'Hare Airport, and it's the cheapest, too at under $3 bucks!!! The blue line Metra trains leave every 15 minutes, and you can get off almost anywhere, or make a connection to another line or train if you need to!
If you want to take a train from Chicago to NW Indiana then the South Shore Line is your best choice. Like its larger client, Metra, it's fast & efficient.
Thousands of Indiana residents take this train into Chicago daily for work & pleasure.
Chicago's El Train is great but if you need to go further distances by train then Metra Rail is your ticket to ride!
Metra's various routes will take you as far north as Wisconsin, to the edge of Indiana, and also out into the western suburbs of Chicago.
Each train car offers double-decker seating and great views in & out of Chicago.