I mentioned the HO for people who dont live in Chicago, @Marilyn. OP said 3 days, never been there. I wouldn’t take in in any city I knew, either.
@lookingforward, I meant that I never knew any visitors who had taken it.
I have read great things about this service; never used it myself : https://chicagogreeter.com/
You could stay in central NJ and visit NYC, Philly and DC in a week. Philly and NYC would be an hour in either direction. DC would be about 2.5 hours
Definitely consider the greeter. We did this abroad and it was a highlight.
But 3 days…the HO covers it in a no brainer way. No finding your own way.
Had I not done this, I’d never have advocated for it. Even between stops, things were pointed out.
Without time, without a car, it’s sometimes helpful to find the right shortcuts. A greeter is often generally one neighborhood or close area.
OP can decide.
Chicago Architecture Tour boat is fantastic, also check out the theater schedule. We got a Chicago City Pass a few years ago—well worth the money. You choose the number of days and pick the places you want to go. Best part: you get a separate entrance and almost no wait time, even in summer. Mostly museums, but also former Sears tower (NO wait—front of the elevator line in the summer), John Hancock, aquarium.
Lots to do—3 days won’t begin to cover all that is available. You can walk (a lot) to most of the tourist area or take an Uber/cab.
We stayed at the Hyatt Place downtown/the loop, highly recommend it. We took cabs to the aquarium and Museum of Science and Industry, but walked pretty much everywhere else.
Are you a parent or a college student? If you are the student, I think you need to discuss the finances of this trip with your parents.
Finances, logistics, preferences of those involved. Start there.
Per OP post #25, sounds like the parents are giving OP the challenge of planning a vacation within a given timeframe and budget. Researching locations, airfares, hotels, etc. can develop some good skills that students don’t always have. Whether this is, “Great idea, see what you can come up with” or “If you want this, you plan it” or something else…
Don’t travel all that way at all that expense and have to worry about not having adequate $$$ to eat nicely and see some things. There are great museums in Chicago - but at a cost.
If your budget is limited I’d be looking at Hotwire or something similar to get better deals on hotels, etc.
Don’t rent a car in Chicago. Take the train or uber into the city and then walk, subway or uber from there. Parking a car would be another expense.
Thanks for the all the advice. I really appreciate your help. As for cities, I was deciding between Chicago and Washington DC. New York seems a little too expensive. The other cities might be best to visit for another time. Thanks @lookingforward for the info on Washington DC. I think I’ll pick Chicago over Washington DC because of temperatures. As for plane tickets, one of my parents might not be interested in going to Chicago so tickets look like their under $900 for late August. Thank you @Marilyn for the suggestion of River North. It seems to make more sense as it is closer to tourist destinations. In terms of transportation, I think we’ll just use Uber since we’ll be doing a lot more walking. I checked the Residence Inn at River North and found it’s about $500 for 3 nights if I book it in advance. Since the hotel has a kitchenette, we can buy groceries and cook rather than eat at some expensive restaurants. All these prices are based on the weekend of August 31st. Is the temperature good at the time or should I wait until fall when the temperatures will be colder? Will plane tickets be more expensive in the fall as well as hotel rates?
You’ve already gotten great advice about Chicago. I will also add that it’s just a fun city to walk around, which is free - the lakefront walk, Navy Pier, Millennium Park, Grant Park, Buckingham Fountain, Lincoln Park (and zoo).
IMO, the Architecture Foundation River Cruise is awesome, but pricy.
Public transportation is cheap and easy in Chicago. No need to Uber and car rentals will just be a pain.
A fun time to consider coming is during Open House Chicago weekend. Tons of historic sites and some museums are free. Not sure what that will do to hotel prices but something to consider: https://openhousechicago.org/
I think it’s great that your parents let you plan a trip! You can save money in an airbnb, both nightly cost and being able to eat meals in…if your parents are OK with airbnb. Also for your travel, the train is cheap and safe, and easy to learn.
I second getting some deep dish pizza, maybe enter some lotteries to see a Broadway show if any are going on (otherwise this would break the budget), there are plenty of comedy shows for cheap and Second City shows are always great. I’ve never been that impressed with Navy Pier, it’s just crowded and not that interesting. The museums are fantastic, you can see the famous Sue TRex, and the aquarium is amazing too.
ETA…I believe the weekend of August 31 is Labor Day weekend…a three day holiday weekend. I don’t know how this will affect travel plans and costs.
Chicago is my favorite city…it has tons to do! Re: weather…@Marilyn is a better source than I am…but there is no easy predicting Chicago weather. It could either be very hot at the end of August, or milder temps.
And I seem to understand now…you are planning this to do with your parent(s).
If you are looking for cooler temps…what about Minneapolis? Another great city.
OP - for me one of favorite thing to do when I visit cities is to try out their cuisines. I would try to few local well known restaurants while you are in town.
You’re looking at Labor Day Weekend which could be more expensive flights and the city will be packed. Also be aware that the hotel tax in Chicago is 17.4% so you have to add that to the room rate shown on the site. It might be quite hot, or not; Chicago weather can vary considerably. Later in September or the first week of October can be some of the most pleasant weather. Also if you’re new to booking flights, airlines sometimes run their sales on Tues-Thurs and fares might be lower than you’re seeing today.
Chicago has great food. Again, if you’re that tight for $$ for the trip choose someplace where you can “Vacation” unless food isn’t important to you. That’s Labor Day weekend and potentially even move in weekend for some schools. If you have the flexibility I’d choose later than Labor Day weekend.
Agree with Chicago having great food; we still miss it. I would not try to economize by cooking in a hotel room. Is there a reason why you want a Marriott property and specifically Residence Inn? Otherwise check out costs for more traditional rooms and enjoy the wide variety of cuisines and prices.
Unfortunately we don’t really try the local food when we visit a new place. Due to allergy issues in the family, we try to stay away from restaurants. This is why we also like finding a hotel with a kitchen or kitchenette so we can cook food. We also found that it is much cheaper to buy groceries at a local market and cook compared to eating at a lot of restaurants.
@thumper1 I am a college student but my parents said I could plan the next trip as long as it is reasonable and the destination is worth it. That’s why I gave out my budget and asked for advise for great cities to go to so we won’t feel like we wasted our money.
@Marilyn Thanks for the info on the hotel tax. I’ll make sure to check the total with taxes than just the rate of the hotel.
@abasket We weren’t thinking of renting a car. I was looking for hotels near the River North area because they seemed close to a bunch of good tourist destinations. We planned on just using Uber and walking.
Did I miss where you are flying out of? I know West coast but I don’t know which airport. Also, what are the ages?
I am in Portland and while it can be very hot at times it is not typically humid.
Once when my kids were 15 and 9 I decided to go anywhere our Alaska air miles would take us. We ended up in Juneau, Alaska. We stayed in a “family room” above a bakery. There was an old frig covered with a tarp in the room…
Down the hall there was another room with a sign, “Bill Gates stays here”.
Anyway!, I have no idea what airfare costs but it was a wonderful choice.
I love Chicago, grew up in Indiana and that was our “big City”. I don’t see flying and staying for 2K.
If you do decide on Portland I will be happy to get involved with guiding you and answering any questions. I think I missed the ages of your group.