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Chicago or Boston?

Ellesmere Port...
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Chicago or Boston?

My husband and I are looking to plan a trip next year for our 3rd wedding anniversary and are unsure where to go.

We'll be travelling from the UK in the last week in August for at least 10 nights but no more than 14. We won't be driving but have no problems walking (we did New York in January and didn't use any form of transport other than our feet)

We like shopping, history, architecture, live music.....basically we love city holidays.

We've been to Boston twice.....we got engaged there in December 2010 and went back for our honeymoon in August 2012, so Chicago would seem like the sensible choice as we've not been before. However, Boston is a very special place and is definately a home from home for us so we're finding it difficult to navigate away from there.

Can people please give me any info with regards to things to do in Chicago/safety/getting around etc? Also, any info from people who have been to both Boston and Chicago would be appreciated.

Thanks

Chicago, Illinois
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1. Re: Chicago or Boston?

If you are coming all this way, go somewhere new: Chicago. All of your concerns have been asked before so type them in the search engine. Chicago is THE city for architecture, dining from hot dogs to haute, look at the stickies in Top Questions on things to do, beaches, dates to avoid - especially dates to avoid since Chicago is so popular with conventions and we have huge events outdoors all summer long that draw large numbers of tourists. If you find a convention or event that draws over 30,000, it will cause a hike in hotel rates. Secure your hotel before you buy your flight tickets. Chicago is that popular.

Illinois
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2. Re: Chicago or Boston?

www.choosechicago.com for ideas of what to see/do here.

Ellesmere Port...
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3. Re: Chicago or Boston?

Fab, thanks for that website. I'll have a look.

Thanks again.

Chicago
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4. Re: Chicago or Boston?

With 10 to 14 days, you could certainly split the time between the two cities. There are multiple flights on multiple airlines between these cities.

S

Bristol, United...
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5. Re: Chicago or Boston?

We've just spent 4 nights in Chicago and can definitely recommend it, we could have spent far longer. The Chicago Architecture Foundation tours are fantastic, especially the river cruise. Do a free tour of the Chicago Cultural Centre, a beautiful interior with a Tiffany glass dome. Walk round Millennium Park and admire the amazing Cloud Gate sculpture. Great shopping on the Magnificent Mile. We spent a whole day in the Art Institute, its collections are incredible. Go up the Willis Tower, the tallest building in the USA and step into a glass box projecting from the side so you look down through the glass floor 103 floors to the street below.

Music is everywhere, from Buddy Guy's blues club where we saw the great man himself, to jazz clubs and the symphony orchestra. In the summer you will also be able to visit Navy Pier and the lakefront beaches.

For a cool, stylish apartment with fabulous views in a perfect location stay in the State & Grand apartments, see my recent review.

California
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6. Re: Chicago or Boston?

My husband and I will be visiting Chicago for the first time too in June. We're really excited, and we've also been to Boston and love that town! He's also from England, and we went to Boston as part of our honeymoon nearly 14 years ago! We had a wonderful time, (even went to Cape Cod and Salem) and he kept teasing me that we owed 200 years of back taxes! ;) (He has since become a U.S. citizen) :)

Anyway, I relate to you having a special place, so I second the idea of doing both cities. A suggestion would be to fly into Chicago, spend most of your time there, then fly to Boston (or take the train, although it's a 24 hour trip and Amtrak isn't as efficient as it is in the UK, but I like trains especially if you splurge for a room) and fly home from there. I believe it's called an "open jaw" flight. You can use the "multi city" option when booking tix.

Whenever we go back to England to see family, and go somewhere else to travel while we're there, we'll always fly out of Paris! Always! Even if we're only there for a few days! :)

Have a wonderful vacation!

Chicago
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7. Re: Chicago or Boston?

tripadvisor.com/ShowTopic-g35805-i32-k700396…

Fairly recent thread on the same subject

Chicago's North...
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8. Re: Chicago or Boston?

go to chicago. august is an awesome time to visit for the reasons mentioned....

podo, if you enjoyed going to cap cod on your trip to boston, then, time permitting, you'd love taking a jaunt to michigan, where you'll find quaint seaside towns, high quality beaches and sand dunes.... having said that, to the OP, with up to 14 days, you could spend 6-7 days in chicago, then do a lake michigan circle tour for the remainder of the trip..... you won't be disappointed.

Rensselaer, Indiana
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9. Re: Chicago or Boston?

To the OP, I greatly enjoyed my visit to Boston several years ago and for the same reasons you mention. Although Boston has a much deeper history than Chicago, Chicago shines in other arenas, as you will see. The architecture, cuisine, theatre and lively arts, music...

For your trip to Chicago, you might look at staying at the Flemish House of Chicago, a B&B located in the Gold Coast neighborhood, if it's within your budget. Especially since you may be here for a greater period of time, you might be able to negotiate a lower rate if you stay at least a week. The location of this is within a few blocks of the top of the Magnificent Mile, close to the Oak Street Beach (to the east) and (to the west) N. Rush Street dining options. This is a really good base for the "downtown" activities as well as expanding to go further into the north side. Yet you still have the close availability of Michigan Avenue, which is a hub for many bus routes going further south (such as the Hyde Park neighborhood, where the Museum of Science and Industry, the University of Chicago, the Frank Lloyd Wright sites, etc. are located).

With such a substantial time at your disposal to plan this trip, read up a little on Chicago's history. Recommend that you look at that Choose Chicago website. Also, research the neighborhoods on the (free) Chicago Greeter service website. If you go to the website of WTTW, Chicago's public television station, do a search for Geoffrey Baer and see the information available on his tours. Also, the Chicago Architecture Foundation and the Chicago History Museum each have tours. You might look into a Chicago History Museum pub crawl, for example - or a tour by 'L by the CAF.

Each of the major museums normally have those "blockbuster"-type exhibits during the summer months. Some do extend past the Labor Day weekend, some don't. However, it is still a little early to be seeing what's in store for next year.

Getting outside of Chicago in the Midwest:

In Chicago, you absolutely do not need a rental car. In fact, it is greatly recommended that you do not get one.

Outside of Chicago, it's a completely different matter. Most of the surrounding area in the Midwest is woefully underserved with respect to public transportation. Most of the smaller towns do not have the availability of any public transportation at all. So, even if you can take public transportation (such as Amtrak) to these smaller towns (such as New Buffalo, Michigan), you really still need a rental car to get around to explore the area, IMHO.

What people need to keep in mind that when mentioning road trips is that foreign visitors not only have the expense of a rental car; but they have to have international driver's licenses (although with the OP it appears to be likely) - and, the biggest expense of all will probably be the automobile liability insurance needed. For some, that might put it over the top of their budget.

One option for a day trip outside of the city, though, might be via the South Shore and South Bend Railroad to the Dune Park station (near the Indiana Dunes State Park and Indiana Dunes National Lakeshore, walkable) or to Beverly Shores, where a person could rent bicycles for the paths. www.nictd.com Look at the information under "Travel" then "Indiana".

If you enjoy horticulture, another option would be a trip to the Chicago Botanic Gardens via Metra (suburban train system) and is a wonderful day trip. You could combine it with a trip to Ravinia, where the Chicago Symphony Orchestra plays during the summer months (until Labor Day weekend). But the concerts there are more encompassing than just the CSO. You can take a look at what they are offering this year to get an idea.

If renting a car is not outside of your budgetary restraints, you could look at a Lake Michigan circle tour mentioned by the above folks - IF you have sufficient time allotted. I personally would allow at least 5 days because I happen to enjoy looking at the sights without a windshield between. (When I was young, my family - determined father driving - actually made it around the Lake in only TWO days. Of course, we never got out of the family car, except to sleep and - well, you know. I'm sure you wouldn't want a similar experience.)

Besides, when you get to the resort communities along Lake Michigan closer to the cities, most of the better lodging places require a two night minimum stay - three on major holiday weekends - during the peak summer month season. The BEST places may be booked up months - perhaps a year - in advance. So it's not as easy as just skipping daily from town to town up and down the shoreline.

My personal suggestion with the availability a rental car from Chicago - for a couple of days, though - would be a trip to Galena, in the NW corner of the state of Illinois. About 90% of the city's downtown is on the National Register of Historic Places. It is *almost* but not quite to the Mississippi River (shy a couple of miles). You can easily combine a short drive along the Great River Road with this stay. Each state has their Great River Road, so the OP could look at Iowa, Illinois or Wisconsin's.

Ballygowan...
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10. Re: Chicago or Boston?

My husband and I were in Boston in 2012 but are visiting both Chicago and Boston late August / early September this year. We like to see new cities but also loved the relaxed feel to Boston, plus the relatively short flight home for us to Dublin. As someone has already said, get an open jaw flight into one city and out of the other for little if any more than a return flight, then get yourself a cheap internal flight direct with one of the US airlines.