Weather in Chicago
 

We were thinking of visiting Chicago for the first time in Sept/Oct. We want to miss the humidity and the heat but also not get the snow. Is the end of September a good time to travel to Chicago and Miss the Humidity/Heat/Snow?

Yes, September would be a good time to visit with more comfortable weather, October even more so.

I like the odds of good weather from mid/late September to early October. Be aware, however, that there are a lot of trade shows and conventions in Chicago that time of year. That will impact hotel price and availability.

The last time I visited Chicago in the fall was in the 3rd or 4th week of October. The weather was beautiful. Might need a light jacket in the evening. I don't remember paying anything crazy for my hotel. I believe it was around $110-$120 per night. My favorite hotel is The River. located 1/2 a block east of Michigan and Wacker. The rooms are a bit small but comfortable.

The odds of snow in late Sep are pretty low to almost zero. The odds are only slightly better for snow during the last week of Oct. The lake water tends to moderate the temp year around in Chicago especially in the fall.

Thank you all for your responses. sounds like that will be a perfect time to visit. can anyone recommend which area is best for staying? we will want to do the museums, restaurants, bars and also Jog around the lake like you always see in movies.

IME, that's a great time of year for Chicago!

Chicago is a very large city offering all sorts of options for travelers with varying interests and preferences -- which means, IMO, that NONE of us can tell you where to stay, what to do, etc. PLEASE get, or at least consult, at least one decent guidebook! The cost will be nominal in comparison to the cost of your trip, and you will learn things you don't even know to ask (and those you do know to ask -- like typical climate).

Good luck!

Ditto to indyhiker's point - when I've been in September, the weather was fantastic, but hotel prices were higher due to lots of events going on. Not necessarily a reason to avoid it - the city didn't feel any more crowded than usual - but hotel prices downtown might reflect that, so just be aware and be flexible if you can.

I prefer to stay in River North or Streeterville, north of Chicago River and east and west of Michigan Ave. I lived nearby and like those areas.

Keep in mind that Chicago is a major convention destination and hotel rates are sensitive to supply and demand.

Between September 10 and 27, 2017, four back-to-back conventions will bring around 55,000 people into the city. There is another large exhibit October 1-4 with an anticipated attendance of 22,000 followed by the Chicago Marathon and related events October 6-8 which attracts another 40,000 to 50,000. Finally, 25,000 convenience store operators arrive October 17-20. If you can't avoid these dates, book a hotel you can cancel, then check back around 30 days before your travel dates as that's when most hotels release rooms they've blocked for the conventions.

To get an idea of what to see and do, check the city's official tourism site: www.choosechicago.com.

For live theatre schedules and discount tickets, check the League of Chicago Theatres site at www.chicagoplays.com.

For transit info, maps a trip planner and how to track CTA buses and trains with a smart phone, go to www.transitchicago.com. You can reach the central city from either airport via CTA train (The L).

For architectural boat tours and walking tours, www.architecture.org.

For other events, concerts and restaurant listings searchable by price, cuisine or neighborhood, www.chicagoreader.com or www.chicagomag.com.

If hotels on your dates are $300-400 range, I'd recommend checking out AirBNB and vrbo in Lincoln Park or Lakeview in a unit that is close to a train station and within comfortable walking distance (as you define it) from the lake.

Look for listings that have been operating for over a year and have more than 20 reviews. Most units will have a license number by July/Aug (many are still pending).

Everything they say about the weather and conventions driving up hotel/apartment prices then is very true. Just remember, this IS Chicago and the weather is completely unpredictable so if you see 90 degree temperatures and snow flurries on the same day don't look shocked. You have plenty of time to have a heart attack over the price of staying some place at that time of year!

What's your budget? That's probably my most important question!

My favorite neighborhoods are honestly the Lincoln Park/Gold Coast/Boystown areas and I've lived all along the lake on the North Side since I showed up here in 1969. These are very expensive areas though.

The far North side (my daughter calls it Rogers Park) can be pretty cheap and even though you hear a lot of crime stories it's honestly not any more dangerous than Lakeview/Lincoln Park etc. My daughter uses this website:
https://chicago.everyblock.com/crime/

Here is another:
http://gis.chicagopolice.org/clearmap/startpage.htm

Many people would disagree but for my personal living situations I avoid the South and West sides. I guess I am a North Sider for life! To be fair my daughter would tell you the West side is easy to commute from and very cheap but I worry every night she spends there. On the other hand, she's still alive after all these years so maybe I am being overprotective or critical? Depending on your budget you decide.

I think staying by any train line at least is good since they all meet downtown and that's where all the things you probably want to see are anyway. It's expensive but our CTA is very easy to use and at least it's reliable before it begins to snow. Another option is to look at places outside the city but by Metra lines because the Metra trains are much nicer, not so much more, and very reliable. They also all come in downtown and some are moments from the city subway lines.

Another question I have is do you need private lodging like a room or apartment or are you open to hostels with dorms, some private rooms, some shared bathrooms, a communal kitchen, etc?

Both my daughter and I always recommend the Chicago Getaway Hostel in Lincoln Park. 1st it's in Lincoln Park, the Fullerton Bus is 5 minutes away, the red, purple, and brown line trains are maybe a 15 min walk, the Clark and Broadway buses are 15 minutes in the opposite direction of the train, and the Diversey bus is 4 blocks away. It's been taken over by a Canadian (?) company in the past decade, completely rehabbed, and is now a very nice, clean, place to stay with a variety of room options. The common areas, like the Tv room, kitchen and dining area are all nice and comfortable and the kitchen itself is professional so you can truly be a master chef if the mood strikes you. There are grocery stores in the area too, a Trader Joe's, a Walmart Express, and a lot of tiny convenience stores. There are also a lot of bars, restaurants, and boutiques around. The management itself couldn't be nicer or more helpful and their prices get higher at that time of year but it's still probably cheaper than other things you'll find.

The other advice I can give for the Getaway Hostel or really anywhere in the city at that time of year is BOOK EARLY or find yourself paying A LOT or out of options.