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The first thing one needs to do in planning a business trip is to do plenty of research.  There are several ways this can be done, but the most popular choice today is the internet.  There are several websites which can offer some of the best deals such as booking.com or wonderu.com, and priceoftravel.com
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Transportation

There are several modes of transportation to be used to get from Milwaukee to Chicago.  You can choose from air, train, bus, or car.  Wanderu.com is a very helpful site when looking for reasonable train or bus fares.  This site can also be used to make your reservations, find out where you would be departing from & where you will arrive at once in Chicago, and your departure and arrival times.

Air, Bus, Train

Air fare is the most expensive and quickest way to get from Milwaukee to Chicago.  Prices I’ve found are from $200 to $250 for round trip airfare on United Skywest or American Skywest airlines.  I personally would not recommend this mode of transportation since the distance is not that great and not really worth it.

Bus fare is more reasonably priced and a more sensible mode of transportation.  Wisconsin Coach Line’s fees vary from $48 to $59 round trip.  Greyhound’s fee for a one way ticket will cost $13.  Megabus will cost $25 for a one way ticket.

Train fare is also another reasonably priced and sensible travel choice.  Hiawatha would cost you $25 for a one way ticket.  I would recommend using wonderu.com, or amtrak.com to make the required reservations.

Car/Parking

If you’re up to the challenge, driving is also another alternative.  Your costs would include gas and parking.  Parking fees vary in the Downtown Chicago area and can be rather expensive.  Spothero.com is a very good website to find where to park, what the fees are per day or by hours, and distance from the hotel you choose to stay at.  Reservations are required and prices vary from $20 to $10 for 3 to 4 hours of parking time.  I found one parking garage that charges $30 per day ($120 for four days), assuming you are returning to Milwaukee on Friday morning.  I would personally try to find parking garages with daily rates.

For those of you who chose bus or train to get to Chicago, here are some suggestions and prices on transportation once you get to Chicago.  You could get around by taxi, rates range from $8 to $11 per ride.  Bus or metro ride are other ways to get around, prices range from $2 to $2.50 for every 1.5 miles.  I would personally choose this method of transportation if you only need to travel short distances around the city.
Where to Stay

I found booking.com to be a very helpful site when exploring hotel costs.  This site also allows you to filter your searches by rate per night, star rating, deals, hotel chains, reviews, room facilities, and more.

Hotels

Hotel costs for a four night stay in Chicago’s downtown area vary depending on what type of accommodations you are seeking.  If you are looking for expensive, luxury hotels such as Wyndham Grand, Comfort Suites, Hyatt Centric, or Four Seasons Chicago, you can expect to pay anywhere between $900 to $1500 for four nights.  If you are more interested in simpler, economic hotels such as Congress Hotel, Hotel Felix, Red Roof Inn, or Acme Hotel, you could expect deals from around $450 to $650 for a four night stay.

 Apartments

Renting an apartment is another choice in where you could stay during your business trip.  Once again, booking.com is the site I found helpful.  The cost to stay in an apartment vary from around $500 to $2600 for a four night stay depend on whether you are looking for simple & economic or if you want luxury.  Some of the more economic places include Millennium Park Corporate Apartments, Bridgestreet, or Oakwood 200 Squared.   Luxury apartments include The Penthouse at Grand Avenue, or Chicago Premier Suites.

Other

Motels or Hostels are “miscellaneous choices”.  I found only one of each in the Downtown Chicago area, The Ohio House Motel at $468 for a four night stay, and Hi Chicago Hostel at $486 for four nights.
Dining

Downtown Chicago has many restaurant choices ranging from expensive, fine-dining to casual, bar & grill.

Breakfast

In some cases, the hotel you are staying at offers free breakfasts to their patrons.  However, if you are not faced with that choice, or you prefer to eat elsewhere, here are some price ranges for you.  According to priceoftravel.com, budget breakfasts in Chicago cost from $25 to $45 for five meals (Mon – Fri).  Suggested restaurants in this price range include Lou Mitchell’s, The Eastman Egg Company, & Pittsfield Café.

Lunch

Lunches in Chicago can be reasonably priced if you know where to go.  Budget lunches can range from $24 to $40 for four days (Mon – Thurs, assuming you are returning to Milwaukee Friday morning).  Some mid range prices for lunch would run from $40 to $60 for 4 meals.  Suggested restaurants in this price range include Xoco, Naansense, & South Branch Tavern Grille.

Dinner

There are plenty of places to have dinner in Chicago that are reasonably priced.   Budget dinners can range from $24 to $60 (for 4 evenings) and $60 to $80 in the mid range prices.  Suggested restaurants in these price ranges include South Branch Tavern Grille, Petterino’s & Xoco.  If you are looking for upscale restaurants, you can expect to pay from $120 to $240 for four meals.  Suggested restaurants in this price range include Mastro’s Steakhouse, Maple & Ash, and STK Chicago.   Reservations are required.

Deals

There are deals to be had for anyone who travels frequently.   I would most certainly check out some the above-mentioned sites, and any other ones you may find.  You should be able to find all kinds of deals on hotels, train & bus fares, coupons for area restaurants, etc, and possibly how to earn reward points, etc.  Enjoy your trip.