Update: Thanks for the advice on not going on Labor Day weekend. I checked Southwest Airlines and found a flight to Chicago for 2 for $750. The departing flight is on the 8th of November while the returning flight is November 11. I also checked the hotel rates and made sure to check the total with tax for 3 nights and it comes to $820. It’s looking good so far. The only thing I’m worried about is I’ll miss class on Friday. I can handle missing a day of class. I just don’t want something like a midterm occurring on that day. So, I can’t really book the trip until I get my schedule and I know airline tickets usually become more expensive the closer you book them to the flight date. The positive side is that it’s in the fall so it will be colder. Is it going to be too cold in Chicago by early November? Does it usually start snowing by then? Also, would it be a bad idea to go on Veterans Day weekend? Thank you for your time and guidance.
Average high temperature in Chicago in November is only 50 degrees, average low is only 39.
Not good temperatures for sightseeing at all. Late September or early October would be much better.
Thanks @Defensor . I’ll try looking in September instead.
Yes, there is a chance of snow in early November (we’ve seen it as early as Halloween). Chicago weather is notoriously variable. I just googled and the average date of the first measurable (1/10”) snowfall in Chicago is November 17. Veterans Day Weekend is not considered a travel holiday weekend like Labor Day so no particular problems. Also remember the later in the year, the shorter the days. It’s really not the best time to appreciate the city but would be more economical for sure. It might be nice but really no way to know in advance.
With Southwest Airlines, you can cancel flights and “bank” the money to purchase other flights. No cancellation or change fees; you just have to use it within one year of the original booking date.
I would suggest a second look at San Diego, especially if you’re looking later in the fall. Mild weather, beautiful scenery, lots of great stuff to do, and health conscious restaurants that can work with allergies. And maybe both parents would come!
@Marilyn I like San Diego too but the family has already been there. One of my favorite destinations was Coronado Island. We’ve never been to the Midwest or East Coast of the United States which is why I really want to go there. I can understand that San Diego is cheaper but I don’t think we would enjoy it as much since we don’t need to actually book a hotel and can drive there and back home in one day. It wouldn’t feel like much of a vacation. As for the time to go, either Labor Day weekend or the week after Labor Day would be best. Going later in September would be getting close to midterms and as for October, I already have a 1 day trip planned and wouldn’t really want 2 trips in the same month. Just exactly how crowded is it on Labor Day weekend?
I would have picked either Washington, DC or Chicago. You seem to like the idea of Chicago. We lived in Wisconsin until retiring to Tampa a few years ago and have spent numerous weekends visiting Chicago. We have also done several DC trips. Feel free to PM me.
Chicago. We usually stayed in the western suburbs and drove to points along the lake. Closer to Michigan Ave is good too. Many hotels offer Fri/Sat lower rates so tourists take the business rooms not otherwise being used. We like moderate places that offer a free breakfast.
Summer is nice- even if it becomes hot/humid. November can be cold and dreary.
Walking Michigan Ave will be among so many other tourists- you can be as casual as you wish like the rest of us. The leaves will be gone from trees by November as well. The definition of cold is relative- depends on what you’re used to.
Oh, the places to see. Navy pier. Art Institute. Museum of Science and Industry. Field Museum. Shedd Aquarium. Lakeshore. Boat and bus tours. How many weeks do you have??? If you have AAA their tour books list so much about the attractions that is easier to digest than an online search can be. You could get a friend’s if need be. You can find out the free admission days. Check to see which special exhibits are available as well- they cost more and can be sold out.
I would aim for August. Days still long and although it may be hot it is still summer and foliage in full leaf. You want to experience the Midwest in the nicest season since it may be your only visit. We planned our PNW visit (high season, sigh) to escape the Florida heat. I don’t recall the outrageous hotel pricing for summer in Chicago. We found a month or more before is needed to get best pricing on travel and hotels.
If you rethink things and decide on a few days in DC that could be easier. We stayed in the suburbs and used the Metro to get to the Mall. So many free (Smithsonian) museums within walking distance that could be more economical than Chicago despite the extra distance. I can’t imagine only a few days in either place if you go to the time and expense of flying.
You have a lot of homework this weekend. Play with flexible dates for flights- can be done on the Expedia website. You can do a proposed dates and see calendars that show costs. Be warned- the lowest fares are for airlines you may not want (Spirit, Frontier for us). Determine how much luggage you need.
@wis75 We have approximately 2.5-3 days to go explore the city. We don’t want to see everything. We just want to see the best things that the city has to offer. As for airlines, I’m kind of leaning towards Southwest. It has some pretty good prices. For the time we would visit, we were thinking about late August and early September. I wanted to go on Labor Day weekend but @Marilyn suggested going later. How are the crowds on Labor Day weekend? Is it better to go the week after? Also, is it hot and humid in early September? Would going in October be more advisable?
Google weather tables. Sometimes you can get an estimate by date.
Traveling for a short time is its own art. Frankly, some people can’t fathom it. But sucess hinges on achieving what you want, without going nuts. Not coming up with a list of sights on opposite sides of a city, unless you allow a proper chunk of time. Not time robbing for morning transpo, just to get into the city. Learning where you’re likely to be near a bus stop, etc. Knowing when you need breaks and what that means to you- lunch or back to the hotel? In a city, planning to have some meals in the hotel room means checking where you can buy the basics.
Only you can assess your interests- and I don’t think we know what those will be, specifically. And what you’d do if it rains.
The only way to figure Labor Day weekend vs another is to look at the feasibility, for you. Compare prices, conveniences, etc. I went in early June and didn’t think it was swarming with tourists. Late August/early Sept may be different, as people do their final vacations before school starts. Plus, that’s the hottest part of summer.
Also, consider the available flights home may leave at some weird hour (esp flying east to west.) You usually need to be at the airport 2 hours early. Or some cheaper flights have multipe stops.
For now, just learn.
@lookingforward My interests are just the top destinations and recommended places to go to. We don’t mind going to a lot of different places. The only thing we’re kind of picky about are museums, aquariums, and zoos. Since there is already aquariums and zoos where we live, we’d only go if it had a bunch of unique animals we wouldn’t see back home. As for museums, we like things with history but we never have seemed to like art museums. Not wanting to offend anybody, but art seems kind of boring to us. I’ve been picking places that are close to each other for the set day so we can save money by walking and not spending too long in traffic going from one place to another. As for the length of vacations, we can do both short and long vacations. It just seems like the vacations that we liked a lot were the ones that were generally shorter. We also find it harder to have longer vacations due to health reasons. I don’t want to elaborate on this due to privacy concerns. I’ll set up a 3 day plan and post it here for tips and advice when I get the chance.
I did edit my other post.
So it sounds like you’re approaching this reasonably. On short trips, I also often skip things that are common at home, unless something about them is the major draw.
@lookingforward I’ve been checking flight times and actually plan to try and arrive 3 hours before the flight. I’m thinking of flying from LAX and Los Angeles is infamous for it’s traffic so one of the hours in the 3 hours acts as sort of a safety in case it is more traffic than we predicted it to be. Would going in October be better? I checked the high on weather averages and it’s 62. The only thing about going October would be that I would need to be extremely picky over what weekend to go as midterms will be around by then. I’m also planning a 1 day trip to somewhere in October so I don’t want to do two trips in one week which severely limits my options. Suggestions on going October vs late August and early September?
Analyzing the pros/cons I get this…
August/September
Pros: Day off from Labor Day; beginning of school year so easy to adjust
Cons: Could be hot, might be crowded
October
Pros: Colder, Hotel cheaper
Cons: No holiday on Monday; Middle of school year; Southwest flight more expensive
This is just my opinion and experience.
My whole impression of Chicago was, “Why didn’t I know it’s this great?” Just pick a date and go, even if you need to change timing of walks due to heat or take a jacket, due to cooler temps. 62 degrees should be a cake walk for someone in the LA area. You take a sweater in case evenings are cooler. Or walk one direction and Uber back to the hotel.
$200 isn’t bad for a room in a major city, you’re looking for something in the thick of things, walkable, and it’s a short trip. Is it two nights/3 days or three nights? I agree having a kitchen is sometimes nice. I have zero idea where you’d get groceries- it’s often a huge issue in a major city. We never cooked, but used the refrig and microwave (I had both in my room in Chi, just as ordinary features. )
You need to actually look at the flight times, both going and coming back. Make sure they work and that they maximize time on the ground. Imo, best is to arrive early, have that day. (The earliest flights are often a great time to fly, fewer lines.) But often, flights back after a productive day are more expensive or book up (business travelers work a full-ish day and fly evening or later.) You need to see, and be prepared to jump.
Sometimes, we do pay a little more for the flight convenience. But how much more? For us, maybe 100 is worth it, (again, maximizing time.) But on a recent trip, the diff was up to 400 more, for the flight we preferred.
Does it have to be LAX? Did you look at the others? It sometimes works to fly from one LA airport and return to another. That is, if you can easily get to/from each airport. Instead of driving and parking, is Super Shuttle still around?
@MoonKnight - if Labor Day is your optimum time, by all means go then. Just be sure to make reservations for any tours or shows well ahead of time and be prepared for crowds. There will be lots of festivals and other events; the end of summer is a much bigger deal in the Midwest than Southern California! You’ll find plenty to do within walking distance of the hotel.
The Chicago Jazz Festival will be in various venues: https://jazzinchicago.org/jazzfest/. Navy Pier will have fireworks on the 31st: https://navypier.org/explore/fireworks/. Riverwalk should be lively: https://www.chicagoriverwalk.us/. It’s too bad you don’t like art because The Art Institute has a stellar collection with some very famous works of art. But since you like history, you could go to the Chicago History Museum: https://www.chicagohistory.org/. If you like baseball, the Cubs will be at home.
There are several grocery stores in River North including Trader Joe, Whole Foods, and Jewel-Oslo (same parent as Ralph’s).
I don’t know about Chicago, but NYC is generally fairly empty when there is a long weekend in the summer because most New Yorkers leave town.
I actually do not think NYC would be more expensive than Chicago. Food can be very good and also inexpensive in NYC. Public transportation is also superb in NYC - you can take a bus to almost anywhere if you do not want to navigate the subway system. Google map can tell you exactly which bus to take. If you don’t like art museums as much (me neither), there is the 911 memorial (a lot of parks along the water), South Street Seaport, Chelsea High Line…etc. A good way to see NYC is to do a hop on hop off tour bus.
NYC is a residential city, therefore there are a lot of grocery stores, from ethnic to Whole Foods/Trader Joe. You can get very nice Airbnb room with kitchen inexpensively. NYC’s weather can be very nice in Sep.
Since you are in SOuthern California, should we assume you’ve already been to northern California (San Francisco)?
Is the travel time included in your three day trip? In other words, if you go Friday to Sunday, will you be flying part of Friday and part of Sunday?
Consider the time change when you make your plans as well.
If you are going to wait until November, I’ll put in a pitch for Phoenix. There is a lot to do there, and if you live within driving distance of San Diego, it’s possible you could drive to Phoenix. Or airfares are not all that costly. In a three day trip, you could go to the Desert Botanical Gardens (do a docent led tour), the Musical Instrument Museum (which is not just for musicians), and a couple of other sites. Good hiking there too. And November is their sweet spot for weather! @ChoatieMom your additions?
You should consider flying out of Long Beach or John Wayne. You’re talking about as little as 2.5 days. Flying East cuts your day even shorter. Flying into smaller, less hassle-y airports is going to maximize your time. You want an airport that can quickly get you into the city you choose. I don’t think that’s Chicago. How about Denver? Beautiful, affordable, easy to get to, lots of good food. I still recommend Portland or Seattle. There are plenty of flights from SNA and LGB that go nonstop to all of those places.
Or how about Vegas? Hot, but not humid. You can get very inexpensive
lodging in the summer, and very cheap food. It’s very bustling, and 2.5 days is probably the right amount of time. There’s a lot to do, and people watching is fun too.
This poster is not looking for a foodie destination…or even planning to eat out much…
How wonderful that you can make this trip! It sounds like you’re focused on Chicago but are still somewhat open. The fares you mention from LAX to Chicago seem pretty high and there are sales periodically. I would set a fare alert with a website like kayak (there are lots of options; Kayak is just one of them) and then you’ll get an email when the fare drops. As someone suggested, include other airports (if they work for you) like Long Beach. Also, Southwest is the one airline that won’t show up on sites like Kayak so watch for their sales too. They do have a low fare calendar where you can see the least expensive time to fly by date. They may also have a fare alert option you can sign up for.
Here’s a link to the SWA’s low fare calendar. Fares start at $92 (one way) between LAX and Chicago Midway in October. If you are able to be very flexible, you could fly round trip for less than $200 per person.
@collage1 Thank you for the low fare calendar. This is super helpful. It’s kind of hard trying to find cheap flights.
The cheapest flight I could find that would also be convenient for us would be leaving on the 6th of September and coming back on the 9th for $730.