The only note I would make about Labor Day weekend in Chicago is that the city beaches will be crazy busy so walking the lake front will be an adventure.
$730 each? For all of you, that’s good. For one of you, I would say you need to find a place you can drive to.
Food, stuff to do, people watching, events, etc… Anyone can do all of those things in all cities mentioned so far.
Hers another interesting alternative. Santa Fe, NM. I have never been, but it’s supposed to be really cool with something to please everyone. It’s not super expensive, I believe. Has a great art scene, beautiful architecture, great food, and a unique vibe.
Do you have a fall break at your school in October. That would be ideal.
I personally wouldn’t choose Labor Day weekend. Chicago is a busy city any day of the year - on a holiday weekend? No thanks unless that was my only choice.
We go to Chicago a fair bit and my son spent several months there student teaching. We got some great hotels via Hotwire - often in the Gold Coast area for around $100 before taxes. If you’re not really picky about hotels (as in a certain brand - of course most of us want a nice hotel!) Hotwire is worth a look - just play around on the site, enter your preferred areas of town (like River North), # of stars you prefer, amenities, etc. - and some sample dates - and see what comes up.
If I"m out and about most of the day I’d rather have more $$ for sightseeing and food (you have to eat out some unless you’re going to go back to your hotel every time you want to eat) than to dump it all into a hotel where I’m going to stay for a couple hours + sleep. Again, I still aim on Hotwire for around 4 starts.
And regarding food is your food budget are small or needs are specialized due to special eating needs we can still recommend very economical iconic or worth stopping eateries that will not break the bank. That’s how we eat!
When looking at flights, you can check to select nonstop. With such a short travel timeframe, you don’t want to lose time stopping or changing flights at interim airports. Also as noted earlier, check the Southwest fares on Tuesday; they may drop from what’s posted on the weekend.
I fly SW most of the time when I fly. Flying on Tuesday and Thursday is usually less costly than flying on the weekend days. Also, avoid commuter flight times as those tend to be more costly.
@Lindagaf It’s $730 in total for two people. That’s for both the departing and returning flight.
@abasket I would love to fly out on Tuesday but that would be super inconvenient for us. Not sure parents would approve because I’d miss a week of school and my classes are concentrated on the middle of the week. Parents would also miss more workdays so it isn’t a good idea.
@Marilyn I was checking non stop flights on the way there. We want to do a bit of exploring on the day our flight arrives. The only problem is that a Southwest flight will land in Midway and that’s pretty far from the hotel in River North. I don’t mind if it isn’t a non stop flight on the way back since we wouldn’t be in any real rush to get home.
As for the day we are leaving, we are thinking the week after Labor Day weekend. Is this a good choice? Also, how bad is the traffic on a Friday afternoon?
First, you do need to say where you are around LA.
There’s a train in from Midway. maybe 20-25 minutes? This is why you need a non-college oriented travel forum. TripAdvisor is like CC, but focuses on travel. It would also help if you more or less told us details and times- like, arriving at Midway at 9am makes more sense than 11am. Unless the 11am is substantially cheaper. But really, think TripAdvisor.
You can leave bags at thehotel, they’ll hold them until you can check in.
@lookingforward The flight that I was looking at would arrive around 1. And I was already planning to just leave the bags at the hotel if we get their early.
As I said upthread and was reiterated, get on Trip Advisor for detailed advice. CC parents are great for helping narrow down destination choices but Trip Advisor is the target website for tourists. They are the experts in travel modes and times and such in the city.
Traffic is horrible at Friday rush hour all over Chicagoland but into the city early afternoon should be ok. You can take the public transit (long walk over a bridge from the terminal) or Uber/Lyft. Unfortunately you do lose two hours flying east but you’ll get them back on the return. Getting in at 1:00 is almost the earliest you can do from the west coast; presume you’re looking at that 7:25 flight from LAX.
The weekend after Labor Day will be better for crowds (and maybe prices) but less events and such if that’s an interest. For regular touristing, though, it’s perfectly fine. Should be easier to get around.
Moonknight- There is a 12:23 am flight on United very very early Friday morning (think like late Thursday night) that arrives in Chicago at 6:24am with a return on Monday Sept 2 on Spirit nonstop from ohare at 4:50pm that arrives in LAX at 7:18pm on Kayak. You can go to the united and spirit sites and book one way directly through the airline. Take note of the small size personal item you can take on Spirit unless you are paying for checked luggage.
With these flight choices you get all day Friday, Saturday, Sunday and Monday in Chicago with only 3 nights in a hotel. You miss one day of school.
On a busy weekend such as Labor Day, make sure you pay for seats at least going to Chicago, and check in right away 24 hours before your flight so you don’t get bumped from the flight!!
Remember, if you spend one extra day in the airport waiting for a missed connection or lose a day due to arriving late in the day and departing early in the morning, you have almost wasted $1000-2000. Make sure your hotel in near the sites or you spend days in traffic, etc.
Have a great trip. We all want you to enjoy this big financial investment.
I’m not sure what I send that indicated you should fly out on a Tuesday. I did ask if you had a fall break - most colleges have an October long weekend break - so perhaps Friday or Monday or Tuesday off with the weekend (or any combo there of) - at least all three of my kids privates did and the uni I work for does. Then you would have to take no days off school.
I feel like the questions you are asking now regarding certain weeks is a little more than we can answer - that’s between you and your family. No one can guarantee a slow weekend, nice weather or the perfect hotel location.
Summary if you are hell bent on Chicago:
- avoid Labor Day weekend for travel on either end and high prices.
- check out alternative methods of booking hotels and getting travel info - like Hotwire, Priceline, Trip Advisor.
- Plan $$$ for some transportation costs. You will likely want to take an Uber or subway (for the experience perhaps?) even if you are still walking miles a day.
- Costs for market food isn’t going to be much less I’m guessing than restaurants and maybe harder to get your hands on. Not like there is a grocery store on every corner! If you want any type of restaurant suggestions - price wise, ethic wise, neighborhood wise - we are your people to make suggestions. (cause you have to have pizza in Chicago - I suggest Pequod’s in Lincoln Park)
Too bad your third family member doesn’t want to come now. Maybe you should choose a location everyone is excited about.
I thought three of you were going, so I’m not sure $730 is great value. Two of you can go to Seattle for three days for $428 RT total over Labor Day weekend. You can both go to Dallas for $326 RT, nonstop, same dates (8/30-9/2.) Those are interesting cities with a lot to do, and they are much more affordable and less time consuming than a couple of days in Chicago.
Your budget is really tight. You can spend your money as you wish, but I honestly don’t think Chicago is a good use of time or money.
Hotel prices in Seattle are very high through September because it’s still cruise season.
@Lindagaf Seattle was a nice option for us but we were already planning to stop by the city for a day or two when we go to Olympic National Park.
You can do a lot on a short trip, even with downtime. But I said, it’s an art. You dont casually back into it without some sense.
My friend and I, eg, spent 2 days in SF. Granted, I had lived there, she had lived in Sacramento, but visited. But 30+ years since. We each picked 2 things we wanted to do, and did them, with walking and looking and absorbing, inbetween. (And a couple of times for Ghirardelli sundaes.) Each day has 3 parts, morning, afternoon, evening.
I only had one day on Chicago, saw a lot. If I (or my family) arrived at 1pm, got to the city by 2:30 or so, we could still do plenty. But not random.
I was mostly forced into it, based on DH’s work schedule. For OP, 2.5 days could be enough for an escape/adventure. But it needs to eventually be more than ‘hit the best parts.’ You have to know what fulfills, for you. And you have to believe, “This is not the only trip to Chicago I’ll ever make.”
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@lookingforward Yeah, I was planning on coming back to Chicago some time in the future. That’s why I’m not expecting to do everything on my list. In fact, I go to most trips with the mindset that I can do this again and go to this place that I didn’t have a chance of seeing the last time I went. As for places, I’m not just selecting random places. I’m looking for places closest to the hotel that would be a good walking distance and places that are bunched up near each other so we save time going from one place to another.
Art museums vary greatly. Chicago’s Art Institute is exceptional. You are playing with so many variables here. Late August, before you go back to school would be a better choice than later fall for the Midwest. When you cross two time zones and spend that much time coming and going you should plan closer to a week. You also need to be much more adventurous with your food. Big cities like Chicago can handle so many ethnic varieties, from mundane to exotic.
What’s this about fall break??? Not where I come from- and Thanksgiving is Thurs-Sunday (exams could be on that Wednesday).
Continue to do your homework with travel sites. There is only so much we can offer. It is not a vacation when a large percentage of your time is spent looking for “acceptable” food. If you only have a couple of days outside the travel time reconsider this big city adventure. Save it for next summer if August doesn’t work for you. A mini trip in the west is better for you if you only have 2-3 days plus a limited budget. High season in Seattle is very expensive, one reason we stay away from the center and go moderate for amenities.
@wis75 Thanks. Like what I said earlier, I’m not planning this to be my one and only trip to Chicago so food isn’t that important. The only fall break for me is Thanksgiving and usually things are crowded at that time. As for travel sites, I’ve been checking Trip Advisor and Expedia but I’m personally favoring Southwest and they only post their ticket sales on their website. I’ll do a little more research on the art institute to see whether it’s worth going. The family doesn’t really like art that much but that is more for designs and sculptures. Looking at paintings is the type of art that we would enjoy.
You know…I’m sure most people would not suggest Cleveland as a destination…but…it has a world class art museum, and the Rock and Roll Hall Of Fame which is really terrific. If you time it right, you could see a show at Playhouse Square…terrific.
@thumper1 Thank you for the suggestion but I’ve kind of set my hearts on Chicago. Cleveland could be a good city to explore for another day on another vacation.