Weekend Trip to Chicago on Amtrak

If you don't like online travel planning - or haven't yet tried it - I'm offering this experimental formula. I've used it only twice to visit Chicago, but both trips were successful - no disasters, relatively inexpensive, and plenty of good memories. I hope these links and tips will help you create an online travel plan that works for you.

I like Chicago, because it's an affordable and stimulating break from my hometown, just 180 miles away. Even within the constraints of a weekend getaway, that's a do-able road trip distance.

Yet Chicago offers a variety of local transportation options, so why drive through city traffic yourself, or incur extra parking costs? It took me years to realize taking the Amtrak to Chicago is a perfect transportation alternative - as long as I'm not in a hurry.

Amtrak

The Pere Marquette connects Grand Rapids, Michigan riders to Chicago's Union Station in about 4 hours for $68 round trip. There are a few stops along the way, but no need to change trains. Passengers tote their own bags, but also help one another loft suitcases into overhead storage when the need arises. This train does fill up.

Tip: get a little something extra for your money if you can. Sign up for Amtrak Guest Awards before you book your tickets:
http://www.amtrakguestrewards.com

Tip: explore pricing for your nearest Amtrak station to your nearest desired destinations:
http://www.amtrak.com/servlet/ContentServer?pagename=Amtrak/HomePage

If you want to compare different dates or cities, the Amtrak website allows you to print various itinerary options. In general, the Amtrak website is user-friendly and will fill your head with dreams of future destinations, too.

When and what?

Next, two interdependent questions: When do you want to go? And what do you want to do when you get there? This is like the chicken and the egg riddle - which comes first? If your dates are inflexible, that's that - book your train tickets and work from there. While some desirable excursions are seasonal (Chicago water taxis run May through August), some places you can enjoy all day, nearly every day (museums).

What appeals to you? Clubs? Festivals? Architecture? Food? Art? Let your R & R tastes guide you through these visitor sites. They provide extensive overviews of tourist staples, cuisine, accommodations, must-sees and maybe-sees:
http://www.choosechicago.com/Pages/default.aspx
http://www.chicagotraveler.com/
http://www.frommers.com/destinations/chicago/0006021097.html

If you like live performances, check event calendar dates within your possible vacation time frames. The www.chicago-theatre.com events calendar site lets you scroll around by dates, check ticket prices, and order your tickets ahead online. If you prefer to keep your options open, your hotel concierge can help you with show tickets after you arrive. In 2006, our Ambassador East concierge reserved Spamalot balcony seats for us by phone at about $60 each. This was just right for us.

If you're already thinking you'll lose your online trip-planning momentum after you're done with this article, order the free Chicagoland Travel Kit immediately. Finding a colorful travel packet in your mailbox a few weeks from now may properly put you back on task: http://www.choosechicago.com/forms/covg_order.aspx

RELAX

Don't overwhelm yourself, because go-go-go is not necessarily the point. List your places to go, people to see, and things to do, and bookmark all of them in one, special browser folder: "Online Vacation 1" (implying it will be followed by a 2).

Print informational websites with phone numbers, maps, reservation confirmation numbers and itineraries. Slide them into page protectors to build your own travel binder - many of my article links became my binder pages. Use MapQuest to pinpoint whatever may be do-able in your timeframe - and specifically, in relation to your hotel address, after you know where you'll stay. All great to have at your fingertips in print after you leave home.

I don't order too many advance tickets. I don't want to be a slave to commitments that sounded good when I was bored stiff at home, but limit my freedom once I arrive. Smart to charge a few potential sell-out events or excursions ahead of time, but engaging public spaces can be savored without reservations or timetables. A nap in an awesome hotel room bed is not a waste. Chances are you'll walk much farther than you expected you would, because everything seems to be "right there" - or else, because you forgot your maps.

Tip: don't forget your maps! Take that binder - it will be your customized guide.

Tip: pack comfortable walking shoes, can't stress this enough. Do not sabotage yourself in the name of fashion. My Skechers added miles to my endurance, but a pair of Borns would've extended my walking wardrobe.

So only after you're sure of your travel dates, go to Amtrak and order the train tickets. If I'm booking far enough in advance, I have tickets mailed to my home. I don't like worrying about a station ticket generator glitch - not that this will happen, just that it can. For me, ticket hard copy solidly in hand, long before the last minute, is a comfort.

Deciding on a hotel

I've had good luck with Priceline: www.priceline.com and Hotwire: www.hotwire.com, but I found deals by selecting the hotel neighborhoods and star ratings I wanted - not the specific hotel. Why do I like doing this? Because I like to gamble, and I'm not yet so familiar with Chicago that I automatically know what I want.

This is not to say you shouldn't consider the advice of those who've already been there, done that. When my husband and I planned our museum trip, a friend who'd lived in Chicago kindly suggested we look farther north for accommodations. She believed the hotels closest to the Museum Campus would disappoint us, so we took a chance on a Hotwire Gold Coast hotel instead. This is how we ended up at the Ambassador East and learned how to use the subway - and we liked both.

So I'm somewhat willing to broaden my horizons by accepting an online travel site's unidentified 3- or 4-star hotel in a recommended area. It's still a roll of the dice, if you do it that way - only after your bid is accepted will you find out where, exactly, you're going.

Most recently, I low-balled on Priceline a month in advance for a Downtown / Loop hotel during the hot summer weekend of July 25 - 27. My $85 per night bid was accepted by Hotel Allegro, a trendy Kimpton boutique hotel located in Chicago's Theatre District. http://www.allegrochicago.com

Tip: all hotels flatter themselves on their own websites, so go to Trip Advisor for the real skinny: http://www.tripadvisor.com/ Valuable hotel reviews written by those who've already stayed where you're about to go mentally prepare you to brainstorm a few "what if?" contingency plans.

Our train pulled into Chicago at 10:30 a.m. and Hotel Allegro honored my early check-in request no problem, at no extra cost. This saved us the hassle of leaving our bags in a Station locker, or in the hotel's possession until normal 3:00 p.m. check-in.

Upon arrival, though, I was disappointed to hear the Priceline rate was based on a room with one queen bed. I'd called ahead for two beds, since I was traveling with a friend, but it had made no difference. We were upgraded to a room with one king bed - which helped - and luckily, the mattress, down pillows and down comforter were all heavenly. So was the big, flat-screen TV. The shower water pressure and temperature were surprisingly good - especially for a renovated old building - and the AC didn't fail.

The quirky décor didn't bother me as much as not having the expected in-room coffee pot - which I understood would be a basic amenity of our boutique hotel. The room was small, but clean and comfortable. The best thing about this hotel was its location, within walking distance of most of our planned stops.

Hotel Allegro's online neighborhood map became indispensable.
http://www.allegrochicago.com/printable.html

Before we left home, I printed it, plotted our walkable destinations, and carried it everywhere with me:

Filene's Basement: http://www.filenesbasement.com

Millennium Park: http://www.millenniumpark.org/

Grant Park's Buckingham Fountain: http://www.cpdit01.com/resources/buckingham_fountain.cfm

and what seemed to be a new tradition bachelorette party hub for local brides-to-be, The Baton Show Lounge:
http://www.thebatonshowlounge.com/baton.htm

Walking to Navy Pier from our hotel the next day was not in our plan. We navigated our way to the water taxi dock, back near Union Station, to catch a boat ride:
http://www.shorelinewatertaxi.com/rates.php
http://www.shorelinewatertaxi.com/

This is affordable and more refreshing than road transportation. Sweltering at the dock awaiting the next taxi can be torture, though.

Tip: pack a sun hat and a UV-protective shirt in your tote.

Although I always wanted to go there, I quickly learned Navy Pier is not for me on a blazing summer day. In July, take advantage of every attraction and / or cruise the Pier has to offer. If you think you'll laze around here people-watching - like you can (and should) at Millennium or Grant Parks - be careful not to have a heat stroke instead.
http://www.navypier.com/
http://www.chicagotraveler.com/chicago-navy-pier.htm

There was minimal shade. Patio tables situated along the pier - except those of the merciful Beer Garden - had no umbrellas. Do scour the Navy Pier websites and plan a hideaway strategy for day trips. Watch for the availability of every next cold drink, before you finish the one still in your hand. The orange creamsicle drink stand situated near the Pier entrance is a godsend.

Crystal Gardens was a spectacular botanical respite, filled with modern fountains and palms. You can even pay homage to a lovable little flowering coffee tree,
http://www.navypier.com/about/ov_crystal_gard.html

but Capi's Italian Kitchen was my oasis.
http://www.eatatcapis.com/aboutus.php

To escape from Navy Pier, try a free trolley - look for signage with the symbols shown on the map link below:
http://egov.cityofchicago.org/webportal/COCWebPortal/COC_EDITORIAL/TrolleyMap.pdf

Of course, free trolleys are packed and boarding lines are long. Trolleys come every 20 minutes, but service stops at 6:00 p.m.
http://www.chicagotraveler.com/chicago-free-trolley.htm

What about a $24 fireworks cruise? Yes, it's a touristy thing to do and once is fun. I had no idea there was a Chicago Harbor Lock until we had to sit and wait to get through it (twice), but our open-water view of the Venetian Night fireworks extravaganza put everything in perspective. Sprawling colorbursts filled the sky and reflective lakeshore structures sparkled.
http://www.shorelinesightseeing.com/fireworkscruise.php

Alternate option: watch the fireworks on foot from Navy Pier and make your cruise a Chicago River architecture tour instead.

Going home

Our hotel check-out was noon, but our train wasn't scheduled to depart until 5:30 p.m., so we still rented Union Station luggage lockers ($12 a day). You can taxi to the Station, lock your bags, and exit via Jackson Boulevard to eat at Lou Mitchell's Bakery Restaurant.
http://www.loumitchellsrestaurant.com/

The coffee was good, the breakfast was fair. I like their weird little citrus prunes and the free donut holes. Mostly, I was mesmerized by the view of the Sears Tower from my sidewalk table.
http://www.searstower.com/
http://www.theskydeck.com/

But we were too late to visit the Skydeck. The service at Lou Mitchell's was slow and, by the time we decided to squeeze in that last tour, I was scared off by the 45 minute wait in line.

Tip: before you wander too far from Union Station, make the Sears Tower your first stop on either arrival or departure day, or just skip the Skydeck altogether and opt for the Hancock Observatory at night instead (nearer Navy Pier).
http://www.hancock-observatory.com/en/

Buying a few magazines to read on a riverside bench suited me better by this time. My friend wandered nearby to shoot her last roll of film. We let our remaining time there wind out uneventfully, left on time, and slept through most of the 4 hour ride home. I doubt my friend would have tried my Amtrak / Chicago weekend formula on her own, so I nominated myself as her guide and introduced her to it in person. I successfully convinced her how easy online travel planning makes it to run away from home, and I'll follow up by making a gift of the binder. Our travel memorabilia is her keepsake and reminder, from now on, that Chicago is really only a few mouse clicks away.