Desperate for suggestions for US trip in August

Have you been to Boston and New England before? Obviously, I'm partial to New England, particularly if you are interested US history. The coast of New England from Boston up through Maine is lovely and often, dramatic, and different than the bits of California coast that I've seen. Southwest flies into Providence, RI...not sure about Logan. Newport, RI and the beaches of Narraganset are also an interesting possibility. From Chicago, I'd head into Canada or just go to M_____ Island (I am blank on the name at the moment, but your Chicago friend will know this old resort island) and relax? For reference, my favorite places in the US are Mt Desert Island in Maine, Newport (and Little Compton) in RI, Boston and San Francisco, oh, and Alta in Utah if skiing.

Or...take a long road trip (or take the train) to Glacier National Park and explore. Pam from Troy can give you some great details about this possibility.

There is a huge motorcycle rally in Sturgis, South Dakota from August 3-12. Now that is something uniquely American to experience!

If you want to enjoy your vacation in the USA in mid August you got only two options - Pacific Northwest and Alaska and maybe parts of California close to the Pacific - I mean very close. Everywhere else is oppressively hot and midwest and east coast in addition very humid.

August is tricky because its so hot in so many places. Northern Michigan or Northern WI would be nice, with the lakes, and close. Depending where on the West Coast your friend is, you could fly there and spend a week in the Cascades or Sierra Nevada, or in Puget Sound or the San Juan Islands, any of which would be my choice--

Since you want to spend time with a friend on the West Coast, consider flying to the San Francisco area. Another possibility is the Seattle and Vancouver area. On the other hand, if I were in Chicago with a car and seven to ten days, I'd drive "The Mother Road", aka route 66 from there to L. A. Parts of the trip might be hot in August, but it is an iconic route.

From Chicago, I'd head into Canada or just go to M_____ Island (I am blank on the name at the moment,

Mackinac Island? Pronounced "mackinaw". Best way is to get there is to cadge a crew job on one of the sail boats in the annual Chicago to Mackinac race. Unfortunately, its in July.

How about exploring the Colorado mountains? Steamboat Springs is fun. Ouray is gorgeous, as Is Durango, and the cliff dwellings at Mesa Verde are nearby. Lots to see & relatively cool temps.

Drive up to Wisconsin. Stop in Madison, see The House on the Rock, visit the Dells, then maybe go all the way up to Door County. It's really beautiful in August.

Fly to Portland, Oregon, then visit in any order the historic Timberline Lodge at Mt Hood (a WPA effort) and the Oregon Coast from Astoria south.

I will put in another vote for that Michigan.

I would do a loop around Lake Michigan, then head up the Upper Peninsula, and back down through Wisconsin.

Here are the places I have visited and enjoyed

Indiana
Indiana Dunes

Michigan
St Joseph
Benton Harbor
Holland
Grand Haven
Traverse City
Charlevoix/Petosky
Mackinac Island (No cars on the island. Take the ferry across and rent bikes)
Sault St Marie (Watch the boats go through the locks from Lake Huron to Lake Superior)
Then explore the Upper Peninsula (the U.P.)

Wisconsin
Hit Door County (one of my favorite places ever)
Milwaukee

Back to Chicago

The Pacific Northwest is an excellent choice for an August road trip. Stretching from the California redwoods up to Vancouver Island, the area it too large to tour in a week. But you could cover the redwoods and Oregon coast, or Washington and British Columbia. Olympic National Park has beaches, rain forest andalpine meadows; Mt. Rainier has wildflowers, glaciers, and the snow-covered volcano. Vancouver is a vibrant city with lots to see. Ferry over to Vancouver Island for outdoor activities. Tofino on the west coast of the island is one of our favorite places, offering beaches popular for surfing, sea kayaking on calmer waters in the bay, and great food.

I know Southwest flies into Seattle. I imagine they serve Portland too, but I did not check.

I agree with everyone that recommends driving north of Chicago. Mackinac Island in Michigan; Door County, Minocqua, Bayfield, and Madeline Island in Wisconsin; and the North Shore of Lake Superior and Ely in Minnesota are all great summer destinations, IMO. In warm weather, my favorite place to be is next to or on a northern lake.

Sam, That's it. I don't know why it wouldn't come to me...all I could think of was Micmac, but those are the Maine Native Americans. Thanks. I haven't thought about that island for years...

As far as humid, yes, New England can be humid, but it is, fortunately, not the majority of the days, if my memory serves me (and I hate humidity), and less so directly on the coast. That is why I like the New England Coast regardless of humidity...those afternoon breezes, needing a blanket at night and awakening to the morning fog horns...
Massachusetts would be the hottest inland, IMO
Jul Aug
Average high in °F: 81 80

Average low in °F: 65 65
Sorry, I just started to wonder what was my love versus facts.

We were in Charleston, SC last August for the eclipse. It gets so humid, the air conditioning in the stores makes their windows sweat! You do NOT want to be anywhere where hurricanes have been historically, not of your own volition. Mainly because you may wish for a hurricane to save you from boiling in the air!

If you're in Chicago in August, it's baseball season! Here is the schedule for the Cubs (home games in blue) and here is the one for the White Sox (home games in grey). The White Sox are playing both the New York Yankees AND the Boston Red Sox in August, so that would be an experience. The stadium is well served by public transport in the city, and you get to walk up with all the other fans.

Having lived in Minneapolis most of my life, my favorite spot for getting away from the August heat was to head up to the North Shore of Lake Superior. You could do a road trip from Chicago, through Wisconsin up to Bayfield and the Apostle Islands National Lakeshore, then Duluth and the North Shore up to Grand Portage on the Canadian border.

EDIT: I spent a week on the North Shore in August many years ago and the temps were in the 50° F. range. It's not always that cool but you could get lucky.

Another vote for Pacific northwest - August is a great time to visit. Southwest flies to PDX. Plenty of awesome routes from there to Cali. Wineries, food, coast, mountains, excellent theater in Ashland, beer. PM me if you decide to come this way I would be happy to help.

If the Pacific NW is on your 'to do' list, August is the time to do it.

There are mountain options and coastal options. Do you want nature, or museums or cities?...or is it all about the road trip?
I know more about the coasts and the Rockies, but as I grew up on Vancouver Island, I will support the Pacific Northwest in August as being fabulous. You could also do some island hopping by coastal ferry in the Gulf Islands that straddle the border. Seattle or Anacortes to Victoria with Olympic Peninsula, various islands....not Chicago or Tel Aviv.
However, New England has great road trips steeped in American history as well as numerous coastal towns with history steeped in fishing or whaling. It is hotter than west coast, but still comfortable.
Oregon is an often missed treasure. Wyoming and the Rockies.
I haven't been but have heard about the beauty of Lake Michigan.
And who wouldn't want to road trip Route 66?
Too many options....all lovely.

There have been a few threads on the Oregon Coast that may give you some ideas. Thread one and thread two and thread three.

Any interest in National Parks? Looks like Southwest flies Chicago to SLC which opens up a road trip up to Yellowstone and Grand Tetons with the possibility of side trips to Cody (wonderful 5-museum complex here) and Beartooth highway. It ~can~ be warm in the days in August but by mid-August it will often be below freezing at night. There will be some crowds but they start to taper off mid-August when kids return to school. It is a 5-5.5 hour drive from SLC to West Yellowstone (West entrance gate) or Jackson for the Tetons. I'd go for at least 4 nights in Yellowstone and 3 in Grand Tetons.

While things book out early for Yellowstone there are lots of cancellations. Yesterday I picked up 4 nights in August at Old Faithful and noted a bunch of vacancies at several of the other villages too. Book only thru the official concessioner. If this is of interest, I'm happy to give you more info than you could ever want, lol!!

On the side, isn't it lovely that everyone loves where they live?! I loved reading everyone's recommendations...of their home areas.

I live in the Colorado Rockies. You can road trip there in a couple days and its on the way to the west coast, or Denver to Chicago flights are frequent and usually affordable as southwest,united, American, and frontier run this route directly.
Weather is great usually, not too hot low humidity. If you are active lots of outdoor activities, (hiking, mountain biking, horseback riding, river activities, fishing etc) many of the mountain towns have various festivals ie music, food, beer, etc.. if you are into something like that.

Yeah, supporting the other Coloradoans who have posted about our wonderful and most beautiful state! So much to see and enjoy from north to south, east to west. Our mountains are simply gorgeous (and there are a lot of them!). Rocky Mountain National Park (and if you're a Stephen King fan, the Stanley Hotel, model for the Overlook Hotel in his novel "The Shining" right at the Park's doorstep) to the north and Crested Butte, old mining town of Durango, Mesa Verde with it's fabulously educational and accessible Indian settlement to the south. It's quite an amazing site. River rafting, hiking, enjoying downtown Denver and Colorado Springs. You could even keep on going south into New Mexico; Santa Fe and Albuquerque are also fabulous destinations with a lot to offer a traveler and not that long a drive. SW has a hub here in Denver.......So many wonderful and appealing choices. Whatever you choose to do, I know it will be a wonderful trip! Oh, and it's cool and lovely in the mountains in the summertime! Yes, Wray-what a wonderful bonus you mention! I definitely love where I am!

JG-- Your statement about a/c is essentially correct as it applies to personal residential property. ( 10-15% of home have a/c)

All commercial establishments, restaurants , hotels etc have a/c.

I have a/c in my home. Many years I never need to turn it on. Only once in 30 years was it on for 3 consecutive days. The nice thing about the Puget Sound area is its rare to not have a breeze and by bedtime its cooled down so all you need to do is have an open window and breathe fresh air.

I lived on the wet side of WA for 20+ years and in Ashland for about 3. Driving right next to the Pacific Ocean is amazing anywhere on the left coast. Mount Rainier, the Columbia River and Crater Lake are phenomenal.

But for me, nothing compares to the mystery and intriguing landscapes of northern NM, southern CO, southern UT and northern AZ. Maybe not this trip, but keep that area in mind for the future.

I live 35 miles outside Nashville. Hey, come on to Memphis and Nashville!!! Yes, the temperatures will be hot in August, but it's only 200 miles between the two cities....and there are not miles and miles of cornfields (that's in the midwestern states).

Lo, I agree about the Southwest, especially southern Utah. But not in August.

Pacific Northwest is my recommendation and I am stickin' with it! Especially since she mentioned meeting up with a friend on the West coast. It it would be nice to hear more from Chani regarding what she is looking for on this trip- cities, museums, art, music, cultural experiences, or scenery, beaches, mountains, relaxation. Actually in the PNW one can get a mix of all. There should be some good music festivals somewhere around here. . . Just need to know dates and we can search.

Similar to others... San Francisco, from there drive Hwy 1 north, along the coast, all the way up to Seattle or Victoria / Vancouver, Canada.

I live 35 miles outside Nashville. Hey, come on to Memphis and Nashville!!! Yes, the temperatures will be hot in August, but it's only 200 miles between the two cities....and there are not miles and miles of cornfields (that's in the midwestern states).

That works if she flies Southwest to Nashville. If she drives down, it's hours and hours of cornfields, soy beans and wind turbines until you hit Kentucky and see some hills.

(Much love to the Illinois and Indiana. We used to make that drive between here and there four times a year. ;-) )

In August we go where the sweltering heat isn't -- the Maine coast. We either focus on the midcoast or enjoy Acadia National Park staying in Northeast Harbor or Southwest Harbor. Bar Harbor gets too crowded.

Thank you to everyone who took the time to make suggestions. I have enjoyed reading them all. I'll start by saying that it's been really helpful and I now have some good ideas to investigate further - either a loop that takes us to Lake Superior or around Lake Michigan. Both are areas neither of us has really explored (including this native Chicagoan). My main concern is how crowded it will be in mid-August. Sam Thanks for the pronunciation of Mackinac. I would not have put it together otherwise.

Both my friend and I lived in the Bay Area (that's where we met), she long-term and me for several years. She now lives in Seattle. Our next-to-last road trip was a loop from San Jose to Monterrey Bay to Hearst Castle, to Las Vegas to Zion Nat'l Park (my favorite place in the world) to San Jose. The last was from Seattle through the San Juans for a week on Vancouver Island and back via Port Angeles. In other words, we pretty much enjoy everything. For those of you who recommended it, I love the PacNW (and spent many happy weeks enjoying it by car) but this time, I'm going to make my friend fly across the country.

Wray I'd love to visit your area (I was in Boston once about a million years ago for an all-too-short long weekend), but it's too far for us this time, I fear. And yes, Glacier is gorgeous.

FastEddie You didn't entice me. TC The only thing that would make me consider Route 66 is if you told me that I'd still see all the Burma Shave signs. There are a few at the House on the Rock.

Charlene and Lola and Pam and andi I love those places, thanks for great memories you have stirred up.

Sarah Please tell me more about Door County. If I go that way, I would definitely stop at Taliesin again, but once at the House on the Rock was enough - even with the temptation of the Burma Shave signs.

Susan and mnannie Thanks for all the ideas. I've never explored Michigan at all. Or Minnesota . . .
Shawn uh, that's the game where a bunch of grown men stand around a big grassy area and spit a lot (why do they all spit all the time?), while thousands of people sit in the sun and drink beer and eat, right? In San Francisco I know they all eat garlic fries, I guess in Chicago it's red hots? Sadly, the Bulls won't be playing - a good friend has season tickets for good seats.

Nancy I'll check out your good ideas too. The only thing I remember well about August in northern Wisconsin is lots of trees and hordes of mosquitoes. But that was many many years ago. Maybe the mosquitoes have gone extinct since then. PS - I even responded on thread three! Love, love, love Oregon.

CL I do miss not being able to go to Ashland. Best theatre outside of London!

Joe Any time is a great time for the Pac NW. Just not in this trip's plan.

Lo The first time I saw Crater Lake was in snow - in August ☺ Literally breath-taking. And you are right, the Colorado Plateau is the best. I am so lucky to have made several trips there . . . but never in August!

Elizabeth I'm already thinking about it for another visit (I get to Chicago about once every two years) - but not in August. It isn't even the heat so much as the thought of long lines at all the sights. And as aquamarine said - it's all the miles and miles of cornfields getting to and from Tennessee. I once drove from Chicago to Dayton and back in August. There was nothing but corn all the way, except for a brief stop in Indianapolis.

I'll also be in Chicago for a couple weeks at the beginning of August. If anyone has hidden gems or local events, please share. I've been to all the obvious tourist sights, most of them more than once.

Doesn't look like it would be a fit for your plans, but nothin' says summer and August like down the Jersey shore. Maybe another time?

Maybe the mosquitoes have gone extinct since then.

Unfortunately no, they are still there but mostly in the interior - do not go to the Boundary Waters area in August.:-) I never experienced them along the lake either on the North Shore or at the Apostle Islands around Bayfield (my favorite Wisconsin small town by the way). They're not such a problem by the water.

All three of the areas in MN/WI/MI that you might be leaning toward are all good for a week's road trip. My personal rating (prejudiced of course) would be 1. North Shore - between Duluth and the Canadian border; 2. Lake Michigan loop and Mackinac Island -although the island is better in spring, early summer, or autumn, crowded in July and August; 3. Door County and Apostle Islands - again Door County can be a bit crowded in August, although not as bad as during cherry harvest in July.

I've been to all three many times and there's lots to see and do in any of them.

If you are interested in the North Shore of Lake Superior, here is the visitor guide: https://www.northshorevisitor.com/
A good town to stay in is Grand Marais.

Duluth, especially the Canal Park area, is a fun place to spend a couple nights. http://www.visitduluth.com/ The blues festival will be going on there mid-August. http://www.bayfrontblues.com/

Another possible stop on the Lake Michigan loop is South Haven in Michigan. I highly recommend the Sherman Dairy Bar there.

Hi Chani!
you've been helpful in my planning my trip to Israel, so I hope I can return the favor! I live in Boston, and I know some folks have suggested coming here, but August can be hot (not by Israeli standards) but very humid, also, weather here is very unpredictable. We just had snow earlier this week. In January, we had several days that were warm enough for shorts!

Last year, my husband and I went to Seattle and Vancouver. It was a great trip, and the weather was so comfortable in both cities. If you're considering a road trip, as some have suggested, I've heard Portland is great too. Great driving trips, amazing scenery (I was astonished at the mountains, and coastline is amazing.

I've never been to the Upper Peninsula in Michigan, but I've been all over the US and Europe, and the scenery and things to do in the Pacific Northwest matched just about anything.

I was just about to write to you about car rental in Israel, I'll do that separately!
Lisa

I just saw you lived in SF, and have "done" the Pac NW. If you want to come East, how about Maine? Portland is a cool city, and there are neat islands. Portsmouth, NH is only about an hour south, and if you hear the weather in Boston is nice, you can make a day or overnight down here, spur of the moment.

Write to me if you want other suggestions in New England. We've lived here for 40 years, and love adventuring, eating, and theater!
There's a lot to do.

Absolutely agree with Igalen. In summer Pacific Northwest or Alaska or both.

Maybe the mosquitoes have gone extinct since then.

After our sun explodes and destroys the earth, the mosquitoes and cockroaches will be the only food for the rats on the bits and pieces of what had been planet Earth.

Bring the high concentration DEET spray!

If it's cool you want, the UP of Michigan might do nicely. I once spent the 4th of July huddled in a tent. Forty degrees. The lovely area Tom outlined in lower Michigan, around Traverse Bay, Petosky, etc, can get awfully crowded in August. You can try the Lake Huron shore. Alpena, Rogers City, Charlevoix. Lovely beaches but fewer people. You could keep an eye on the weather-always changeable there. If it's cooler, stay in the mitten, if it's getting warmer, go to the UP. You can swim in Lake Michigan and Lake Huron. Not Superior.

If it's photo ops and bragging rights you want, go to Hell and then Paradise, both in Michigan.

In Indiana we get these ads a lot. https://www.youtube.com/watch?v=6YMNlRJ7AF0 They always catch my attention.

Before kids and before they charged an admission fee, we spent an afternoon on the porch of the Grand Hotel, drinking gin & tonics. https://www.grandhotel.com/

You can swim in Lake Michigan and Lake Huron. Not Superior.

Not strictly true, there are places where you can swim in Lake Superior. There are a few beaches in and around Duluth MN and Superior WI where you can swim in July and August. Water is still cold, but not freezing. I have spent a day on the beach at Park Point in Duluth when we swam in the lake without freezing our ___s off.

Another vote for Michigan here. Lots to see and do. South Haven is close enough to Chicago that you can stay at a B&B then continue on up the coast of Lake Michigan. Dunes, lighthouses, little towns and beauty everywhere. For something else here is a "Route 66" you can consider. http://www.pbs.org/video/road-trip-route-66-ko1n3e/ Under the Radar is a PBS show that features towns and points of interest throughout Michigan. You can catch a ferry to Mackinac Island from Mackinaw city (both pronounced the same). Cross the Mighty Mac (Mackinac Bridge) to the U.P. Drive over to the locks at Sault St. Marie, see the Pictured Rocks National Shoreline. Visit Tahquamenon Falls State Park. Drive west on M-28, the Seney Stretch. Some say it is exciting as driving across highways next to corn fields. I could go on but I wouldn't want to overwhelm you with all of the awesome things to do in the Mitten.

One idea that has not been mentioned is South Dakota. Yes, there is the big motorcycle rally in Sturgis in the west part of the state. There is also Mt. Rushmore, the Black Hills, Devil's Tower in WY, Jewel and Wind Cave, Custer State Park, the Badlands, the Pineridge and Rosebud Indian reservations. There is the South Dakota Dinosaur Black Hills Institute of Paleontology. There is the Mammoth Dig where hundreds of mastodons died in a lake. In Sioux Falls, there is Hot Harley Nights, where we sit around and look at motorcycles. If you let me know when you will be coming, I will guide you around some of SD, in return for you guiding my wife and I around Israel. It's about a 10 hour drive from Chicago. On the way, you can visit the House on the Rock, southern Minnesota, Devils' Lake, and other parts of WI.

How about either:
1. Glacier National Park - SW flies to Spokane, it is about a four hour drive to Kalispell. Or you can take Amtrak from Chicago to the park and on to Seattle.
2. Yellowstone National Park - SW flies to Boise with a five hour drive to the park.
Actually the MI itinerary looks good and is driveable. After seeing the locks at Sault Ste. Marie, you could cross into Canada and drive to Niagara Falls, then back to Chicago.
Ed

You could leisurely do a loop from Chicago to Madison WI (where if you like music there are any number of outdoor venues for free music, including the UW campus lakefront Student Union), then drive north on 1-94, stop at the dells of the EauClaire County Park in Plover WI, (Skip Wisconsin Dells, but do drive through Devils Lake State Park). Then head east to Door County. Drive through Green Bay and stop at Krolls (for chili, pie and/or a milk shake). Door County is now about an hour away. The West side of the peninsula is very busy with traffic, but if you drive through the middle and east side near Lake Michigan, much less crowded. Door County has 5 state parks and 19 county parks. Cave Point County Park is a 'must see.' If you like lighthouses, this is the place for you. Aside from the beauty of the Door, there are many art galleries to visit. My favorite is Edgewood Orchard Galleries on Peninsula Players Rd, Fish Creek. Once you are done with Door County you can drive south to Manitowoc and take the SS Badger ferry across Lake Michigan to Ludington, Michigan. I saw a good list of Michigan sites on a prior post. Highly recommend Sleeping Bear Dunes National Lakeshore. Drive south through Indiana and back to Chicago. OR, if you can't stand the thought of that trip (because the traffic at the lake in Indiana is very heavy) instead drive to Muskegon Michigan and take the faster ferry to Milwaukee, then drop down to Chicago.

I lived in and near Green Bay and Madison for several years and still visit friends annually...been to Door County many times. If you have any questions, feel free to PM me.

There will be cheese.
And mosquitoes.
Just think of the humidity as a warm hug.
And beer. (Great Dane for food and beer in Madison)

With 52 replies, you should now have at least one recommendation for each of the 50 states.

Now why would Chani want to skip the wonderful Wisconsin Dells?? Perhaps she has not seen enough tshirt shops, fudge shops, cheese shops, and all in one place?

Fun group activity in a place like the Dells or Gatlinburg or Branson- Everyone spend just $5 and see who can buy the tackiest souvenir.

UPDATE

Again, thanks to all of you for your suggestions, some of them so very tempting, others intriguing, and many for consideration on a future trip. Yesterday one of my Chicago friends torpedoed my original plan by giving us 4 nights in her timeshare just outside the Loop (Dearborn/Harrison). That leaves us only 3-4 days to fill, probably to Galena and/or Taliesin - not sure we can manage both. If you're familiar with the area and have suggestions, I welcome them.

And if you have recommendations for Chicago - other than the obvious sights - either downtown or near north, bring 'em on. No baseball, thanks.

Chicago in the summer - must go to Ravinia! Take a lovely picnic, sit on the lawn and enjoy the show. We lived up there for several years and it was one of our very favorite summertime things to do.

Galena is lovely, too. Especially if you like wine. :)

Thank you Celeste, I'd completely forgotten about Ravinia. Please tell me about Galena and wine . . . .

Galena wineries

It's been ages since we were there so I don't remember which we visited, but it's such a cute town and I recall the wine being pretty good. I was probably less discriminating then, so don't hold it against me if you find othewise!

Thanks again. If it's reasonably good, we'll drink it. We are not connoisseurs.

I love Galena so that would also get my vote.

Chani, if you like Frank Lloyd wright.... a nice day trip from down town Chicago is to Oak park, you can either take a tour of wright studio and home, or do an outdoor tour of 15 buildings he designed. Both are lovely and I think cost about 30 dollars apiece. You can take the commuter train out to Oak park, maybe a 30 minute ride. Downtown the loop, navy pier, art museum and aquarium are all good

doric 8-thanks for the info about Oak Park. I didn't know about it and am adding it to my bucket list.

I haven’t been since the late 90s so am not sure what it’s like now, but Lake Geneva and it’s boat tours was always a fun excursion not far from Chicago.

I also used to enjoy Galena when I lived in that part of the country.

https://www.cruiselakegeneva.com/boat-tours/

cala - if you're interested in Wright buildings, there are several in Hyde Park too, including guided tours of Robie House, across the street from the U of Chicago. I don't know if there are any guided tours of the neighborhood, I saw it with a Chicago Greeter.

Everyone - thanks for all the great ideas. We're pretty well set on Galena/Dubuque and maybe Prairie du Chien.

Dubuque has a lot of lively low cost options, make sure you ride the "elevator to the top of the hill and check out the Mississippi river museum. 2 colleges in town might offer some fine arts performances.....

Chani, as we were planning our Aliyah, I had to see a few thing before leaving forever. So a couple of summers ago, we went to Chicago. Really loved it and because we are architecture buffs, we did the whole FLW house and Oak Park. It was really great. The Chicago Architecture Society does these amazing walking tours all over the city; I did like 6 of them! If you go to Taliesin, we'll be so jealous.

Can not believe I'm just reading this post.. Sorry Chani!
So look into the Chicago Architectural tours.. In August you must book ahead!
We lived in Oak Park and currently have a condo downtown. Sounds like you know Chicago fairly well, but I learned a lot on a CAT tour.
The botanical gardens in Glencoe or Morton Arboretum (western suburbs) are a quiet place to get back to nature.
In August, there is nothing like a day on the beautiful Lake Michigan beaches.
If you are into history... check out Pullman, IL, very interesting.
If you have a rental car and want to get out of Chicago, I would suggest driving to our beautiful SW Michigan and spending a night or two. We have so many wineries and now we are listed as one of the fastest growing micro breweries areas (we even grow the hops). There are companies that provide the transportation to visit many of the wineries.
Chicago can be stifling hot in August, but the lakefront is almost always cool.

Chani - I see that you've made your choice! I hope you'll come back later and tell us how it went?