Im a 29 year old woman and am planning my first trip by myself in July. I cannot for the life of me decide between Boston or Chicago.
What I'm looking for...with a budget! =)
-a place where i do not have to rent a car and can depend on decent (and safe) public transportation to take me about anywhere
- definitely a downtown hotel where i can experience an array of things to do and see walking distance without the price killing me
-parks where i can possibly have picnics
-relaxing beach to visit
-down to earth bars, young adult scenes
-can't stand humidity but from what i heard both cities have it- less would be preferable
-museums, art galleries, theaters are not a priority but surely would be enjoyed
-an active night life that doesnt necessarily have to be dance clubs

Very hard decision... help! =)

Both cities have everything you want. Both are wonderful cities.

Doesn't make it any easier, does it?

So here is some minor stuff that may make a difference:

Boston has a 5% sales and meal tax, Chicago's is higher. Both have outrageous hotel taxes, and both have excellent public transportation.

If you like to shop, there is no sales tax in Massachusetts on clothes (well, any item less than $500).

It is faster to get into Boston by public transportation than it is to get into Chicago.

Boston has wonderful harbor cruises. There are cheap water taxis, and the cruise to George's Island and back is a great way to spend a hot afternoon. Chicago has actual beaches on the waterfront, but it lacks harbor activity and interest.

It may all come down to where you can get the cheapest flight.

Be sure to use Priceline to book your hotels. It offers substantial savings for downtown hotels in my experience.

Chicago WAY bigger, may be a good thing or not....

Boston, definitely less humid, on average, than Chicago

Probably easier to go to beach in Chicago, Boston on ocean but not exactly on beach

Bar scene in Chicago is probably a hundred-fold that of Boston, but how many can you go to on one vacation?

Chicago a great city, but Boson is like no other place in the US....

(I grew up in Chicago but moved to Boston in my 20's)

You will enjoy either place, but they will be very different experiences....

Staying in downtown Boston anywhere around the Freedom Trail (Fanueil Hall area, waterfront, North End) enables you to walk to a wide range of historical sites, restaurants, bars, harbor, parks, museums, concerts. Subway/streetcar rides to most other interesting places like the Museum of Fine Arts, and the Isabella Stewart Gardner Museum. Boston is a blend of the old and new, going back to the early 1600s. IMO the most interesting city in America to visit (not in winter).

For lodging, and done more than 6 weeks to 2 months "out"/before the trip, from Priceline or .hotwire or .quikbook- Chicago will have better rooms at cheaper pricer than Boston 90% of the time.

Distances in Boston are miniscule compared to Chicago- and if you plan somewhat ahead or ask the natives re like a Rachael Ray kind of attitude- you will find great food at cheaper prices in Chicago, IMHO.

Also, if you are flying in- the ride to any downtown location from the airport can be done on the Orange Line from Midway VERY cheaply- no taxi. Something to consider in the mix.

Boston is extremely walkable. It offers you the harbor, the Charles River, the Public Gardens. And Cambridge across the way.

You could also take the commuter rail to Rockport for an afternoon of quaint seaside village.

That said, they are both fantastic destinations.

The blue line from O'Hare is also very cheap (about $2.50) and easy!!

I'm closer to Chicago so I get there quite frequently. Love Michigan Ave area. There are some really nice hotels and restaurants, and of course the shopping is hard to beat. I also love the Chicago Art Institute and the other lakefront museums. Each one is worth a visit.

I get to visit Boston (for a fodors GTG) in the fall and always enjoy myself while there. I have seen a number of the historic places but still have a long way to go!

Either choice will be a nice vacation.

My vote is for Boston, due to all sites being close enough to walk to and/or easily done by public transport. If you want beaches, take the ferry to Provincetown. Logan Airport is also well served by public transport
www.massport.com/logan/getti_typeo_mbtas.html

Thanks for all the input! Is the humidity really that bad in Chicago Mid July? How are evenings like?

Also, I was looking at Priceline and it offered different areas. By the descriptions given, I think I like either
a. the Millenium Park, Loop and Grant Park area
and
B. North Michigan Ave-River North Area

any thoughts or comments about which area is better?

Also, If i for instance stay in the North Michigan Ave-River North Area, would you know how long it would take me to get to the Millenium Park, Loop and grant park area?
by foot?
by public transportation?

thank you!

I would guess a 25 minute walk from River North to Millenium Park (a great urban park with outdoor concerts). Going there via Michigan Ave. will be pleasant. There are many buses that go up and down Michigan Ave.
You don't need a car in either.
Both cities have what you listed:

Chicago-great nightlife, best I have seen outside of NYC.
A Beach in the city that you can walk to from North Michigan.

Boston-easier to manage by walking alone. Places for picnics but no beach in the city.

North Michigan Ave-River North would offer the better hotels and more active nightlife.

Do one city this vacation, the next the next vacation! I admire you for vacationing alone.