Originally Posted by Ryansox

Not in any particular order but these are my opinions of each
1.The W Lakeshore I used to love (pre covid) always recieved an upgrade to their Marvelous 1 bedroom suite overlooking navy pier. Post covid the benefits went downhill, I had to fight them to get breakfast as a welcome amenity not once but TWICE. It is like a 5 minute walk to navy pier however.

2.Hotel Chicago Downtown doesn't really have suites or upgrades per say, but they do have a lounge on the 1st floor that is (was as of Jan) open on the weekends and they also allowed us to get additional guests in for free.

3.Chicago Marriott Downtown I've gotten some pretty suite upgrades at but they don't have an open lounge on the weekends and they are exempt from providing breakfast when lounge is closed.

4. Ritz Chicago is worth the upgrade IMHO, they treat all their guests wonderful. We got upgraded on a points booking memorial day weekend this year and loved it. Suite overlooking navy pier. They do give titanium members a discount card for 20% all food and bev, 20% gift shop, and 10% spa. We ended up eating dinner that night at their Italian restaurant and breakfast again in the morning with the discount.

5. The Gwen is nice, we didn't get an upgrade the weekend I stayed but the breakfast that's included was good. I thought this hotel was much nicer than the Chicago Marriott Downtown which is located nearby.

6. Marriott Marquis Chicago (while not on your list) it is attached to the convention center and not near anything really it is worth noting if you don't mind uber/lyft or driving around. Stayed here over a dozen times and receive upgrades EVERYTIME to their top of the line suites with amazing views of the skyline. The views at this hotel especially at night with the skyscraper skyline and lake Michigan make me return every time. They also do have an open lounge (it opens at like 6 or 7 and closes at 3pm daily) and they do let you get guests in for free.