- Linda McMillin reviewed 3 years ago
It just seemed like one of the races one should do – running through wine country that we have visited for over 20 years – what could be better! Getting into the race is quite the adventure! The first year, I tried the lottery with no luck. The next year was even more entertaining. The signup just happened to be on the same day we were driving from Park City Utah (home) to Moab for the Winter Sun 10K. Bruce drove as I tried to enter on my iPad as we drove by the Bookcliffs in Southern Utah – not very good reception through there! Needless to say, I didn’t get in. But, I made it in 2014! I am so glad I did. By then it was my 7th DR race – not bad for a girl from Utah! The weekend started with the Welcome Reception at Cuvaison Winery – the race start! Saw our DR friends and met new ones – the racers you meet are all so inspiring! Then, the big event – meeting Meb att the pre-race dinner! He is a treasure! So humble and so inspiring! The race exceeded my expectations! We ran through beautiful, rural Carneros Valley. It was stunning! Rolling hills (little ones) and beautiful vineyards. It was a perfect, foggy morning to run! I was inspired by all of the Team Challenge runners! And then there was the Guinness stop and the wine stop along the way! But, nothing prepared me for the finish – our flag flying high in front of the Sonoma Plaza!! This has to be on everyone’s bucket list of “Not to Miss” Half Marathons!
- Amanda S reviewed 2 years ago
- last edited 2 years ago
What a fantastic race! I strongly recommend this series to all levels of runners and can’t wait to sign up again next year.
-Super affordable (3 races for under $50!) and the nature of a series does wonders for my motivation.
-Very well organized! RunwithPaula does a fantastic job organizing races – runners are well taken care of (water, food, sports drinks, coffee and MORE). I’ve been running for a couple years now and have never bothered repeating a race. Her events always leave me ecstatic and grateful to have spent the money.
-Excellent series for hitting your PR! I shaved a ton of time off over the three races.
-Easy course with no delays from traffic. Good views through a grassy area next to a pond and no pavement problems.
-Great energy from all involved. I’ve never enjoyed a post race party so much (great awards and raffle)
-Beginner friendly with lots of speed walkers.
-Starts a bit later in the day than other winter races, making it so much easier to get there.
-It’s a bit of a hard run to start. The first 1/4 mile is through a road passing several office buildings. On the flip side, on your way back it certainly makes the finish line look like gold in the distance.
-Due to flooding (a 2″ thick puddle) you are asked to run up a VERY small but VERY muddy hill, which caused one or two people to slip.
-The course is public so there were a couple slow moving older couples and zippy bicycles to circumnavigate.
-I took the no phones/timing devices rule very seriously on the third race and was left a bit sad to not have music to listen to.
- Sarah Gamble reviewed 2 years ago
- last edited 2 years ago
Yes this last years Pints to Pasta had some huge issues with the shuttle, I was super grateful to have chosen to run the half marathon distance so the shuttle was a non issue for me. I love running downtown & really enjoyed the course! The after party was great with a nice meal, beer & wine. I loved this race and hope people give a little grace for the traffic/construction/shuttle nightmare, I’m sure they will make this race better than ever next year! I can’t wait to do this one again!
- Mariah Jeffery reviewed 2 years ago
- last edited 2 years ago
This was my first marathon in 2015. I loved that the course went uphill for the first half and downhill in the second. The course was very scenic and also very shady. The biggest issue I had was that I had memorized where the aid stations were supposed to be, and took my gel at mile 6 expecting an aid station at mile 7. It was actually at mile 8, and the volunteer handing me Gatoraid when I asked for water. Still, for the price it was an excellent value. The race was run very efficiently and the shuttles in the morning were on schedule and no hassle. The food afterward was great also. I will be doing the half this year.
- SqueakMatteson reviewed 2 years ago
- last edited 2 years ago
This is one of those races that you will be bragging finishing about for YEARS. People will have to listen to you talk about it every day for at least a month afterwards, because that’s the minimum time it takes to forget the pain of running through several miles of ice-cold, ankle-deep Northwest lake clay. This is a true trail challenge, and a foolish venture if you’re not prepared. I did the 25k, which takes place the day after the 50k runners tear up the trail and make it good and sloppy. This would be a challenging run even without the mud; the trail is single track and technical. There aren’t too many elevation challenges, but elevation will be the least of your problems, thanks to the sloppy, slippery, constant thrill of running in mud. You get a break from the mud on a small stretch of paved road, but then you’re right back in the slop. Seriously — check out the race photos from previous years. They tell the tale.
The aid stations will go down in history as some of the best — gels, fruit, candy, peanut butter sandwiches, and a nice selection of hydration drinks. Volunteers are friendly, there’s a real Hagg Family vibe going on, and race directors are very responsive to runner questions.
One caution — if you break your stuff on the course, like I did, it can be a treacherous limp to the main road to hope someone comes by and gives you a lift. Hopefully they’ve improved upon that, as the year I broke my ankle on the course I had climb to the main road and wait for help until a woman drove by looking for her husband, and she ended up picking up a few of us gimps without intending to (super nice lady!)
Packet pickup is easy, shirt is nice, and in the past you got some cool finisher’s socks. I think they started giving out medals, but that started the year I broke my ankle and there ain’t no socks, medals, or swag for the DNF-ers. Very well organized, a beautiful setting, and a crazy hard run. My ankle didn’t heal right so I won’t be doing it again, but I am glad that I did.
- Jay Ricker reviewed 8 months ago
This 5k is the best! I took my young children and they had a blast! The staff and volunteers are extremely friendly and they go the extra mile to make everyone feel welcome and appreciated. We will definitely be signing up for this race every year from here on out!
- Ashleyaob reviewed 2 years ago
Eugene half/full continues to be one of my favorites! It is always pretty competitive and appears to be very well run. I ran the full a few years ago and had a great experience, so I was not surprised that the half was just as great. My one comment/suggestion is for the race to have more water at the finish line. I know the race strives to be as green as possible, so no need to have plastic bottles, but some cups with water would have been great.
- running favorites reviewed 3 years ago
The one thing wrong with this race is that it’s too good! You’ll need to sign up quickly once registration opens. The course is fast with a few rolling hills. It’s exceptionally well organized, plenty of porta-potties at the start, along the course and at the finish. The wine festival after the race is really great in the lovely Sonoma City park. Although run in July, the morning starts are almost cool, if not even chilly.
The Race Director has done a great job in attracting top running celebrities (Ryan & Sara Hall, Dick Beardsley, Meb Keflezighi, Bart Yasso, Tesfaye Alemayehu, Sergio Reyes, Lauren Fleshman and many others) to run the race and/or speak at the Expo.
This is one of the top half’s in the country – don’t miss it!
- coverbeck reviewed 3 years ago
I have done Rock n’ Roll Portland three times. In 2013 and 2014 I did the half marathon. This year I did the 10k. What draws me to Rock n’ Roll Portland is the size and energy. Anytime streets are closed down and 30,000 people are running through my city, I just want to be in on the fun! The music and masses of runners out to just “rock n’ roll” creates a fun atmosphere. Although, they have an elite program which draws many good runners, the race is catering to the athlete that is just out to have fun and accomplish the distance. However, with the energy that comes with the crowds, you can make it a serious competition if that’s your goal. The course is not a fast route as there are several hills and a lot of turns. However, the diversity of the course keeps you engaged and is a good way to see some great areas of Portland. The course goes over several bridges which are unique and fun. If you are a runner that loves to make a day out of a race, then Rock n’ Roll is a great race. There are plenty of free goodies at the end and music to listen to as you relax.
I had a great time at the St. Mary’s 5k last year, and I’m looking forward to it in 2016. For an inaugural run it was very organized, and packet/shirt pickup was smooth. The run was a nice route that took you through downtown Stayton and out on to a pretty river trail. It was well-marked, and supported by happy volunteers all the way. The thing I liked best about this race was seeing the families out enjoying running — I purposely held my pace back in the last mile just to watch a young family encourage their mom running her first 5k; the joy was infectious. The registration was relatively inexpensive, and I liked the cotton t-shirt with a cheerful graphic on it — not fancy, but when a race is a fundraiser for a school, you can’t be a jerk about “perks.” There were port-o-potties at the start, but I don’t recall any on the route. There was a water station staffed by happy, encouraging volunteers. It’s not hilly, but there are sections of trail which aren’t challenging but aren’t paved. I had trouble finding water at the finish, but it was a small, inaugural run, it was a minor glitch.
This race is a staple that every Oregon runner should do at least once. It’s an established event with a long history, is organized, has a large field of runners at all ability levels, and might be one of your only opportunities to see someone blast past you wearing lederhosen. The course is rolling, with some climbs, but then you get the opportunity to make up speed on the downhills. The optional tech shirt is usually of decent quality and won’t break the bank if you add it to your registration. The start can be crowded as you weave through the streets of Mt. Angel after starting out in a park, but then you’re out in the countryside around the Abbey (which is worth a visit for architecture buffs, as the library was designed by Alvar Aalto) and the crowd thins out a little. I noticed two porta-potties on the course, but I think everyone was in such a rush to finish and get into Oktoberfest that they didn’t stop to use them as I didn’t see lines. My only quibbles were that the course monitors got ignored by the drivers in a few spots, and things got a little nerve-wracking as disrespectful hillbillies sped by. Oh, and some potholes, but I can trip on thin air so maybe that’s just my problem. The age group awards are generous (new achievable goal! Oktoberfest AG Ribbon!) I found parking along the main road in front of the Fest Halle, and there was plenty of room for everyone, but I did have a little bit of a walk to the start–if you get their super early you can find a spot in town near the start. Most importantly, we got FREE BEER and entry to the Oktoberfest, which was AWESOME. Even my German-American “I hate running” husband enjoyed himself!
I signed up for the 5k this year due to a date conflict with running the half (which I hate to miss because it’s a very pretty run) and was pleasantly surprised with the fun atmosphere and big crowd turnout for the 5k. Packet pickup for any of the Iris runs is very smooth if you do it before the race; the Keizer Chamber of Commerce stays open way late and makes it easy to get your gear, but I can’t comment on race day pickup as I have never had to use it. This year we got a nice cotton shirt (which I was thrilled with — I’m a little tired of tech shirts.) The 5k is an out-and-back along the parade route, and I was not expecting such a big crowd to already be in place for the parade and cheering on the runners — that was a real treat and made it a very festive (albeit overcast and chilly) morning. There was a nice cross-section of running abilities in the race, and tons of families getting out together to run. Which is sort of a mixed blessing; this was the most kid-populated 5k I’ve ever done outside of the Girls on the Run events, so be prepared for a ton of little ones who haven’t learned the race etiquette intricacies of things like not stopping in front of people. It was fun to see kids everywhere, but it wasn’t really fun to try and not fall over them when they dart in front of you and stop to verbally harass their slower siblings! Luckily there was space to get around the wee ones and stretch out to enjoy the flat course. There were plenty of porta-potties at the start, and I was surprised to receive a medal at the finish, which was in addition to a lovely cut iris bloom. Chip timing readouts were available in the tent at the finish with minimal wait. About that tent — it’s got pancakes and breakfast snacks in it! Everyone’s a winner when pancakes are involved!
- Melanie reviewed 2 years ago
- last edited 2 years ago
My friend Sarah told me about the race just a few days before hand, and I decided to join her! I was very pleasently surprised with the price of the race, especially since I was registering so late! The morning was COLD, probably the coldest race for me so far, and I was so thankful for the hot coffee at the start of the race. The 10K was two loops, clearly marked, and separated the 10K and 5K runners so that we could easily keep running. I actually enjoyed the loop so that I could plan and conserve my energy for the hill in the middle of the course. Overall, I was very pleased with the race and definitely want to do it next year! Oh, and I loved the medal!
- smokeybailey reviewed 3 years ago
- last edited 3 years ago
By far, the Destination Race in Santa Ynez/Solvang has been my favorite half. The scenery is beautiful and includes bison, cows, horses, sheep, goats, llamas, alpacas, longhorn, and my favorite, a turkey at mile one…just right on the street, hanging out. Only in Santa Ynez. The race IS hilly but was fast for me. Last year I PR’d in this race and this year I was right at the same time. I didn’t use the porta potties, but there are TONS. Also, plenty of water stations-every 1.5 miles or so. Last year was hot so they came in handy. The miles are well-marked and the race is easy to follow.
I love this race because it’s small. It doesn’t take long to get started at all. I’ve been in races that took easily 20 minutes for my wave to get started. I didn’t run with a pacer but they have them for just about every 15 minute interval up to 3 hours. The organizers are great and friendly. They remembered my crazy husband from LAST year! We did the finisher’s party at Lavender Oak and it was a lot of fun. Beautiful out there. If there is a wine tour post race, do it! We did it last year and had too much fun.
There is a post race wine and music event, which is great but we did find it too crowded so we didn’t do it this year. Post race, we typically need to rest a bit and we found the area too small for the number of people who were participating but it’s a great deal. I highly recommend it to runners who don’t really need to recover after the race. It’s a good price for all the beer or wine you can drink. I plan to sign up for the one in Oregon when we run that one.
Santa Ynez Valley is great for wine tasting. Even if you don’t tour the area (which you REALLY should), there are tasting rooms in Solvang, SY and Los Olivos every 10 feet. You can’t go wrong.
Also, if you are a single guy, this is YOUR race. Tons of chicks out having a good time and drinking lots of wine. My husband tells every single male runner he knows that he should really be coming out to these races to meet cool chicks who like to run. It’s a great run for groups of girls or couples (like me and my guy). We are trying to talk two friends from Alberta, Canada into joining us next August in Oregon. It makes for a great long weekend.
In the past I’ve done the Mustache Dache in Corvallis and found it to be a super fun, festive event with great energy, so I knew I wanted to do it again this year. I signed up for the Portland event, just to mix things up, and HOLY CRAP ON A HOCKEY STICK this course was a RODEO. They are marketing this event ALL WRONG. It’s not a 5k, it’s a MARCH UP THE SIDE OF A MOUNTAIN. The first two miles or so are an unrelenting climb — sometimes steep. I saw people stopping to lean on recycling bins. Folks were sitting down on front lawn landscaping boulders. There was no break from your journey directly into the sky until you hit the top and started the STEEP downhill and prayed to your ancestors that you didn’t tear your tendons out of your shoes trying not to go flying into the side of someone’s house. It was nuts, people. Just nuts. They really need to re-brand this into a Facial Hair Hill Climb 5k Hellfest or something, because if you can run this whole thing without dying you are a SAVAGE BEAST.
Packet pickup was fast and friendly, shirts were great, and sized appropriately. If you were freezing you could hang out in the awesomeness that is Big Al’s. Plenty of port-o-potties. Small vendor turnout. Big, happy crowd. You get to run alongside a pack of Tom Sellecks. Booze and a few of the usual snacks post-race. One complaint — you had to hunt down water after you finished (and were over being curled up in a ball, clutching your quads, and crying) and then they ran out and had to find more. Medal was a cool, and holy cow YOU EARN IT.
I don’t recommend this as a “first 5K!” because it will make you hate running, but if you want a challenge, put it on your calendar for next year.
- SqueakMatteson reviewed 1 year ago
Signing up for this race was an experiment that turned out better than I had anticipated. I was super curious to see if racing in the evening as opposed to the a.m. would have a deleterious effect on performance, so I signed up to find out. And to be completely honest, I signed up because all of the race swag would have owls on it. I love owls. An owl medal? OHMYLORD yes. Gimme one of those! Pre-race instructions were clear and plentiful, and I had originally signed up for the 1/2 marathon but was able to switch to the 10k with ease. Traffic on I-5 getting to Vancouver was as expected — terrible — so if you sign up plan on getting to the race as early as you can. Even if you get there ridiculously early, Vancouver Lake park is just a beautiful place to relax and wait. Parking was easy and well-managed. Race day packet pickup was quick, with one quibble — if you went to the picnic table on the left, you got to pick from this year’s or last year’s shirts, and if you went to the table on the right, you got the current year’s (and a little bit of attitude if you asked for last year’s.) I like to have the dates and places on shirts, and none of the shirts did. At least my tank top has an owl on it, that helps ease the pain. And the owl glows in the dark, which is super nifty. Pre-race instructions were clear and delivered frequently. The supercool Last Rites drum corp was there to get people motivated and ready to run. There was an option for an early start for the half marathoners, which, as a turtle, I always appreciate. The running path was well marked, and the park is absolutely beautiful. There were almost no elevation changes save for one short uphill sprint at mile threeish, and the path was decently maintained. There were plenty of aid stations on the 10 and 5k routes, I suspect that the Half was also well-equipped. Volunteers were cheerful and helpful. The park path was narrow, and after the 10k turnaround it became a bit of a parking lot in spots, with 5k walkers (and 10k walkers who thought the early Half start was also for them) three to five abreast across the path. I felt bad for the speedsters, as they had a lot of zig zagging added to their workout. Names were announced crossing the finish line (Huber Timing always does a great job) and the medals are adorable. Also no date or location on them — another small quibble. After the race things got a little confusing, as you had to go get a cup of water from a small table that was mobbed. I had water in my closely parked car so I skipped standing in line for water and instead got in the superlong burrito and beer line. I guess they ran out of beer early, but I waited patiently and chatted with other runners as the line moved slowly forward. There was a live band playing, and the location was perfect for stretching out on the grass and enjoying a cool Saturday evening. I will do this race again, but will bring friends and plan on running a shorter distance, as I’ve discovered that evening running is not going to produce any PRs for me personally.
- sheri reviewed 2 years ago
I’ve run the Seattle half a few times, and it’s always been a great experience. Packet pickup is held downtown over two days and is painless enough. The shirt is long-sleeved and technical and is accurately sized. The race itself is always held the Sunday after Thanksgiving, which is either awesome (it’s a great fitness goal in a pretty gluttonous time of year, having 13 miles in your near future helps you say no to that third slice of pumpkin pie on Thanksgiving) or not so awesome (it’s an early Sunday wakeup after a long and relaxing weekend, having 13 miles in your near future makes you say no to that third slice of pumpkin pie on Thanksgiving), depending on your perspective. Also, have you been to Seattle in late November? The weather is extremely iffy. I’ve run this race with clear skies and in sideways sleet both. Luckily, this year was great – dry and cold.
Race morning this year was very well organized. The run started almost exactly on time, and the beginning of the race, through the downtown streets, is a great way to start – a huge sea of people filling up 5th Ave all the way through downtown. From there, the course goes over the freeway, through a gorgeous waterfront neighborhood, through the leafy arboretum, and then back through another neighborhood to re-cross the freeway and end in Memorial Stadium. There were plenty of well-stocked and not-too-busy aid stations, and lots of places for supporters to stand and cheer us on. The course is fairly hilly, but none of the inclines are both steep and long. The finish was well thought out, too, with quick access to water and space blankets. Overall, a great race, and one I’ll do again.
- Brock M. reviewed 8 months ago
Perfectly organized. Some of the great things about the race is there are very generous donors that offer great prizes to win and there have been tons of (actually really nice) goodies that came with the registration on race day. The course is new asphalt trail. Lots of families racing.
- Run Oregon Blog reviewed 3 years ago
In my second weekend of back-to-back races, the inaugural 2015 Volcano Half Marathon exploded onto the scene and into my heart on Sunday, May 3, 2015. This race, put on by Run With Paula, was everything a new race should be: well-organized, unique, measured, and fun. And Paula knocked it out of the park.
After competing in the Sisters Better Half Marathon and Bend Marathon and Half in late April, and the Willamette Mission Trail Challenge on May 2, this race was the culmination of 4 races, 8 days, and 45 racing miles. I wasn’t necessarily tired, but I was just a bit sluggish. The perfect temperatures and blue skies were a natural remedy and elixir for a weary morning – and it didn’t hurt that the race was in my hometown as well.
The finish of both distances (half and 5k) were at Volcanoes Stadium, the home of the Single-A Minor League affiliate of the San Francisco Giants. Volunteers were extremely helpful through the quick registration and packet-pick up lines – a theme that was very prevalent throughout the course of the event.
Following the quick shuttle ride to Willamette Mission State Park, we all took off into the quiet and peaceful rural streets of unincorporated Keizer. This is an area I am very familiar with, as I have done many a training bike rides out on these roads. We got to pass hop farms (including a farm owned by Hood River’s Full Sail Brewery), red clover fields, and farmland as far as the eye could see.
While the course was not closed to traffic, there wasn’t much motorized traffic at all. In fact, there seemed to be more race personnel and local fire/police assistance than anything else. I never felt unsafe at all. The hill around mile 4 was a bit of a challenge, but we quickly headed downhill shortly thereafter and continued with a steady straight course. This portion of the course, I was also very familiar with, as it is a running route AND the reverse direction of the Keizer Iris Festival Half Marathon loop that has been around for a handful of years. The last few miles spit us back out into civilization for a straight stretch on Lockhaven Dr. and some neighborhood streets before the stadium came into sight.
As I mentioned initially, the organization and support were fantastic.The aid stations were never an issue and they appeared with great frequency. Additionally, the volunteers were amazing. Everyone was paying attention, smiling, and some were even blowing bubbles. obviously Paula’s happy demeanour had rubbed off on everyone!
After the race, we were treated to a free hamburger (hotdog or garden burger), drink, chips, and cookies – as well as standard post-race faire. Live music by the Ben Rice Band was providing a great auditory background as we waited for results soaking up the mid-morning sunshine.
If you haven’t run in Keizer before, I highly recommend this race. If you haven’t run a Run With Paula event before, I highly recommend this race. If you like quiet, rural runs to lose yourself in the serenity of, I highly recommend this race.
In summation, I HIGHLY RECOMMEND THIS RACE.
View full results here.
The next Run With Paula event is the Independence Day 10k, which takes place in the city of Independence and the famous Rogue Brewery hopyards.
- SqueakMatteson reviewed 3 years ago
- last edited 3 years ago
This is a fun event, very big and they do put a lot of effort into making it festive and enjoyable for runners. Packet pickup was smooth, course suppport was adequate (bring your own gels) lots of volunteers. Tons of porta-potties, and if they see half the crowd standing in line they’ll wait a few minutes for you. No wave or pace start, so be prepared to mow down the walkers who march right to the front of the line. Nice relatively flat course, but be prepared for some grumpy North Portlandites who curse out the volunteers directing traffic and try to gun it through the intersections. The shuttle system worked fine, but can get a little backed up. After party is crowded but fun, soup was tasty. Loved the shirt and the medal. In the past I’ve missed the cutoff date for the “fancy” shirt, and tried to exchange the “latecomer” shirt for the “fancy” one, but despite the piles of leftover “fancy” shirts you’re not allowed to exchange. But you can buy the “fancy” shirt the next year for $5.00. Seems lame if you just paid $90 for the race — give a bro a shirt, y’all!
- Ashleyaob reviewed 3 years ago
The Shamrock experience is always a good one. I have run the 5k for the last 3 years in a row and enjoyed it all three times. However, I probably won’t do it again. The race directors bill the 5k as a “run” and not “race,” so maybe that is why they do not pay too much attention to the finish. From mile 1.5 onward, the 5k runners are mixed into a sea of 8k runners. Which means for the last half of the race the lead 5k group is weaving in and out of slower 8k runners. It is pretty difficult to find a straight path and actually race it. It seems like an easy problem to solve – divide the road into two parts: 5k and 8k. Especially in the last 800 meters or so. Anyhow, it is always fun to be out there and participate, but I will either do one of the other events or skip it next year.
- Tyler1447 reviewed 2 years ago
Clark County Running Club annual Vancouver Lake Half. Capped due to parking makes this a more intimate race at 475 entries. Low entry fee cost with the option to buy one of the best tech Ts I have received from races the past 2 years. I find myself running in these Ts more during the off season than any others I own. Water stations seem to be further apart than I like, but they were well stocked and I was good on the course. I have run this race in 2015 and 2016. For whatever reason the finish line water was limited to one 8 ounce Costco water bottle per running….not nearly enough. But, the porta pottys are plenty as are the volunteers who really make this an amazing sellout event. Oh, and home made cookies at the finish!! Hard to beat that.
- Erica Endicott reviewed 2 years ago
- last edited 2 years ago
This was my favorite race to date! Amazing course, beautiful scenery, very well organized and bananas on the course(BRILLIANT. Finishing on Hayward Field on the Jumbo Tron was amazing. The after part was so well organized, no lines, lots of water and food and no lines. Would receommend this race to anyone wanting to run a half or full marathon.
- coverbeck reviewed 2 years ago
- last edited 2 years ago
This is my third time doing the Chicago Marathon. I’m drawn to the race because of the energy and size. Never will you feel like you are just out for a training run- the energy and crowds will remind you that this is the day you’ve trained for! I love how the whole city of Chicago seems to rally around the marathon. Of all the marathons I’ve done, the crowd support in Chicago is by far superior. However, with this energy comes the tendency to start too fast- be careful of that!
The Chicago Marathon is a pancake flat course expect for a small short hill at the end. However, I’ve learned that flat is not always the fastest. Some inclines and declines can be nice to switch up the muscle groups. I’d recommend doing some long flat concrete runs to prepare the legs for the repetitive motion and pounding. The other thing is that Chicago is called the Windy City for a reason and the weather is unpredictable. It’s always a gamble if Chicago will be fast conditions but I think it’s a worthwhile gamble.
With the participant size of the Chicago Marathon come the perk of lots of people to run with and water stations go on for a whole city block and are every few miles. You never have to worry that you will miss an aid station.
As for after the race, I can’t think of a better city to enjoy! Bonus: you won’t feel weird hobbling down stairs after the marathon because it seems like half the city is as well!