I totally agree with Chicago in the Fall. You can fly Southwest to Midway and take the train in. Often Southwest has some great airfare deals.
I personally would not want to fly from the West coast to east coast to stay only for 3 nights. Just doesn’t sound time or cost effective.
Not sure what are you looking for in a “big city” vacation. But with your limited budget, perhaps Sacramento could be your vacation for three days. A few museums, Salmons in Sac River and Drive around or hiking in Tahoe are all fun to certain people.
Thank you for all the suggestions everyone! So far, I’m interested in Portland, Chicago, and Washington DC. They seem like nice places to visit. I wouldn’t mind increasing the budget a bit to accommodate all our needs. To be honest, this is the first time I’m planning a vacation. What would be an appropriate budget if we flew to Washington DC or Chicago in the fall? I know airplane tickets are generally cheaper on Tuesdays but it’s hard to find something that is both cheap and convenient. As for hotels, my family and I would also like to stay at a 3-star hotel for 3-4 nights. We actually like short vacations every now and then so I wouldn’t mind exploring the city in just 2-3 days.
Won’t you be in school between September and November at your dream school?
What do your other family members say about where they want to go?
@abasket No, I’ll be attending there in the spring so I want to go somewhere before I attend. Plus, I wouldn’t mind taking a Friday or Monday off in the fall for a 3-day or 4-day vacation. As for my family members, they’re letting me choose if I can budget it and spend wisely.
Hmmm…interesting. Have you asked the other three vacationers where they want to go? Are they young like you - or older?
@abasket Parents, and they don’t mind since they’re letting me choose as long as I budget it and spend wisely. When I mean spend wisely, I mean pick the right place at the right time that is worth going to with lots of wonderful sights. Basically, a place where we would get our money’s worth by going.
If you are going in the fall, New England is lovely in October. Boston itself has some of the higher hotel prices in the country, but if you head from the airport (Boston Logan or Manchester) to NH or VT, I suspect you can find Airbnbs at good rates if you book early, but as @Lindagaf said, leaf peepers will be coming. You would need to rent a car if you are flying.
In the summer, SF is downright cool (two weeks ago, driving from Palo Alto to SF, the temperature dropped 15 degrees and we went from sun to fog), but I love Marin County and north. We have spent magical times near Point Reyes.
I’ve never spent much time in Midwest cities except on business, but I’d guess that Minneapolis and Madison WI would be nicer in the summer. Others would have to advise you what to do there as tourists.
You pretty much can’t get into foliage New England or the major cities in fall. Not without preplanning and many have booked already. And not for cheap, unless it’s uncomfortably so. Don’t forget the budget includes food and any places that do charge admission. If you rent a car (eg, to see foliage,) add that cost. In any city, parking $ can be nuts, even at a hotel.
Chicago is amazing. If the only thing you dois the Hop On/Hop Off bus and go up the John Hancock tower, you’ll get the sense of the city and the beauty of Lake Michigan. But remember that staying in the burbs and taking the train in or renting a car and needing to park add to cost.
DC is splendid. But don’t go in summer or early fall. It’s in a basin and miserably hot and humid.
1-2k is tough. If you haven’t done it, consider the drive from south of SF through Big Sur. It’s easily a family thing. Other than that, based on the budget, Portland sounds good. Look into the train that goes up the coast to Portland.
We have a number of travel threads, but generally asked by a parent, who already understands the logistics, costs, tolerances, etc, and is often already looking on TripAdvisor for more info.
Actually, I have found good deal/nice places to stay in greater New England, but not as simple as flying into Boston and there’s one right there, between the airport and the city, at the right price. And not all will be near transpo.
I’m reminded that when a friend and I booked maybe 2+ months ahead, from Bos to Sacramento (where we’d first see friends, before SF,) it cost each of us about $450 RT. We thought that was good and it was much cheaper than into SF or San Jose. When we booked rooms down the coast (September) we had some nice but simple rooms for around $200/nt. But 3 nights would be $600, a chunk of your budget.
I think I’m leaning towards Chicago. From what you guys described, the place seems amazing and I’d want to go check it out.
@lookingforward I made a document where I calculated the budget of everything except for admission and food. I found plane tickets for 3 around $1500. I’m also planning to change the hotel I picked to something cheaper. I’ll be looking at cheaper hotels when I get the chance. As for transportation, I was thinking of just using Uber and walking as we’ll only be exploring for 3 days.
For the people who went, is the river tour by boat worth it? What other locations would you recommend? I’m mainly interested in Magnificent Mile and the Chicago River Walk. How safe is the surrounding area as I’ve heard that Chicago is a generally unsafe place? Also, I heard that my budget is kind of small. What would be an appropriate budget if we plan to stay for 3 nights?
How many people and for how long. Oh I see now…3 people…3 days.
$2000 will cover your airfare, and either a rental car or Uber. You need to allocate money for lodging, meals and some things do cost money to get into.
Summer is an on season travel time except for places where it’s HOT which you say you don’t want.
There is ONE of me and I’m going to Cleveland for five days. It’s costing just me about $1000…and I am staying with relatives.
If you can drive…I would second San Diego. So much to do there…and take airfare and rental car out of your budget and you might be able to deal with lodging and meals for your family on your budget.
Just FYI…Chicago can be both hot and humid in the summer. Someone upstream suggested DC. If you don’t want hot or humid…don’t go to DC in the summer.
If you go to Chicago see if you can get Hamilton tickets there. Pricey but well worth it.
@thumper1 I said I don’t mind increasing the budget a bit. What’s an appropriate budget for Chicago in the fall? And it’s 2-3 people for 3 nights.
I did some research on hotels and Residence Inn looks like a nice place to stay. I checked and found the studio rate to be only $202 a night which is pretty good. I have a tough time deciding however which Residence Inn would be better to go to. Which is better, the one on Magnificent Mile or the one on River North? Any suggestions would be much appreciated. Thank you.
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If flights cost 1500, that’s 1/2 to 3/4 of your budget.
The only two things one needs to do, first and foremost, afaiac, is the Hop On and the Hancock (a stop on the HO bus.) The view from the top is more than 240 degres. Astounding. And the HO bus shows you all the primary points of interest. You can get off, see something, get back on another bus (or return later for a museum or whatever,) if xx or yy interest you.
I was there one day and loved it. I did the bus, got off at 3 spots, then walked back to my hotel. Mine was on Michigan Ave, bu the Art Institute. (Free, using Marriott points.) Read the Residence Inn reviews, look at photos.
As a tourist, unless you take risks, you likely won’t notice any “dangers.” I found people very friendly.
Over on the Magnificient Mile/Michigan Ave, you can find cheap eats. Places like Panera or whatever. Apparently Chi is known for hot dogs- I hadn’t known how close I was to some famous venue.
(Sorry I keep writing Miracle Mile. That’s in LA.)
Chicago is a great tourist destination except during winter, which is why we moved to San Diego!
Portillo’s for hot dogs in Chicago. Garrett’s for cheese/caramel corn: https://www.garrettpopcorn.com/ Eately is a fun place to grab a bite or a meal: https://www.eataly.com/us_en/stores/chicago/ Chicago Architecture Tour for boat tour: https://www.architecture.org/tours. The Hancock Building has great views but if you want to save a bit of money over the Observation Deck https://360chicago.com/, you can go up to the Signature Lounge for a drink instead: https://www.signatureroom.com/lounge/. Tell your mom to check out the view from the ladies room - seriously.
The most centrally located Residence Inn would be the one in River North, where you can walk to tons of destinations., including the River Walk and the Art Institute and the lakefront.
We lived in Chicagoland city and suburbs for 40 years and never knew anyone who took the Hop On Hop Off.
What kind of activities does your family enjoy? There are world class museums, top restaurants, excellent theaters, and upscale shopping, and lakefront beaches. https://www.enjoyillinois.com/explore/listing/chicago-museum-campus
https://www.msichicago.org/ https://www.artic.edu/
Not sure where you’d be flying from but Southwest goes into Midway Airport which IMO is more user friendly than O’Hare.
Avoid the weekend of the Chicago Marathon, October 12-13. Also large conventions can affect hotel prices so take a look at different weekends if you’re seeing higher prices than you like.
FYI you might try Trip Adviser with your questions on specific destinations as you narrow down your choices - tons of local experts there.
My kids and I took a family vacation to Chicago a few years ago. We loved it. We flew into Midway and bought an unlimited transit card for a week. We took buses and the El everywhere, or walked. We stayed in an airbnb in Lakeview which was a block away from the main bus routes and a short walk to the El. We went to the Art Institute and the Science museum, walked around Navy Pier and Grant Park, went to the beach for a day (it was August), visited Northwestern, ate deep dish pizza, ice cream and at a great vegetarian diner. We didn’t take the tourist bus or go shopping. I’m sure that we spent less than $200 per day, including the Airbnb.
Forgot to mention Lincoln Park Zoo, which is free: https://www.lpzoo.org