My plan is to leave from Chicago with my car and backpacking gear June 21st and I have to be back by July 23rd. I also have to be in Vegas from July 1st to July 4th. The rest is all time for driving, backpacking, and exploring! Also I'm a bit of novice backpacker but in excellent shape, but I probably won't be doing anything too long (nothing longer than a week). But anyway if you were me what area/trails would plan on hitting?! Thanks

Gila Wilderness, New Mexico - beautiful and isolated

You might want to try the Porcupine Mountains in the Upper Penninsula of MI, just east of the border with WI. Easy to get too, easy to get a permit, just drive up and ask, beautiful country but not so deserted that you won't see anyone. Of course in late June and July, the bugs will be fierce but that is true just about anywhere.

When "bugs are fierce" I go to the coast or desert. Anywhere windy is good. No coast between Chicago and Las Vegas, so that leaves high desert. How about Zion? Escalante?

Bah. Bugs are fierce at the nicest times in the alpine! when all the flowers are out!

If you can't deal with bugs and a bit of snow you miss good stuff

I will take snow over bugs any day! One of the few times I actually bailed out of a trip was for bugs. Moderate bugs, I can handle; fierce with bugs - I leave.

you have many options, but the first decision is which highway system you will follow, or whether to stay off highways altogether. Since Chicago is sort of north you have your choice of I80 through Wyoming, the southern highway 40, or anything in between, as well as a junket above the border into Canada. Since you're coming from Chicago you might enjoy the southern route and doing some desert trails, OR getting in some mountain time - and if so cross through Colorado. Zion and that Utah bunch of parks, and the Escalante area, offer some very different terrain than you are used to seeing.
Jim

Canada would be quite the diversion for you though. not that
the very bottom of Alberta/BC around waterton isn't nice, but
you can probably get similar nice stuff in Wyoming (wind rivers) without getting as far out of your way going from chicago to vegas.

If *I* were you I might think about Zion or Gila in new mexico as mentioned though, but that's just because I do rocky mountains all the time up here. doing desert for me would be different and I haven't been to those places

The year I visited the Porcupines in Michigan's UP in mid-June, my dog and I nearly were eaten to death by massive swarms of flies! It was too hot to stay in the tent. I loaded my dog into the car, drove up and down local roads as fast as I could with the windows open to blow out the flies, then shut the windows and drove around with the air conditioning on until dark. Repellent didn't seem to have any effect. If you're going there in June, wear a headnet, long sleeves, long pants and leave the dog at home!

The UP in August, on the other hand, is wonderful!

Well my tentative plan is to take I70 through Colorado and Utah to get to Vegas. I'd like to hike around in Rocky Mtn Natl Park for a few days, although I have a feeling it will be hard to get a permit. Then I think I'm gonna do a few days in either canyonlands or escalante assuming I can take the heat. After Vegas I'd like to head up through the Sierras, then take the high road home through Idaho and Wyoming and take I80 back to Chicago. I was hoping to kind of wing the trip, but that seems to be a bit tough to having to get all the back country permits and stuff, so we'll see...

If you backpack in national forests instead of national parks, you don't need to bother with backcountry permits, except in a very few high-impact areas (such as the Enchantment Lakes area of Washington). The most you'll need to do is to fill out a form at the trailhead. IMHO, the scenery is just as good and there are usually a lot less people!

I agree with mouse, there are plenty of great places in the west with no quotas, I avoid national parks. You will like Escalante... The Burr trail was great when I was there.
Jim

I will chime in with mouse and shaw, and I enjoyed a forty year + career with the National Park Service. I always had a fondness for Forest Service wilderness areas (hence my response nominating the Gila Wilderness).

If you are going to go where everyone goes, you must reconcile with the hassles of the permit system. If you are willing to take the road less traveled, permit issues will largely vanish.

Permits and paperwork in the Gila Wilderness have actually declined over the years I have been hiking there.

That early in the season, you might be fine in RMNP, especially mid week.

I'm surprised nobodies mentioned it, but if you're coming back through WY, it would a sacrilege to not visit the Winds.

Then again the Beartooth's are right there as well.

No permits required for either.

Choices, choices, and so little time.

I agree about the Winds. But I don't know if the trails are gonna be passable. Currently, the Winds have a higher than normal snow pack. Some places are still reporting 200%+ pack. The OP said they would not be into Wyoming until mid to late July. I think there's just gonna too much snow up there still.

If you're coming through Colorado, avoid RMNP like the plague. Stay out of national parks and take advantage of all the incredible wilderness areas. If you're into fishing, try the Flat Tops. They'll be almost snow free by the time you'll be there.

Or I would recommend the Weminuche Wilderness. It's huge. The backpacking options are unlimited. And for pure ruggedness and beauty, it rivals RMNP but minus the crowds and regs.

For complete isolation, head to the West Elk Wildernesss. You'll have 1000s of acres all to yourself in June and July.