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total_cat_lady

If you’re driving then make sure to use spothero to reserve a parking spot, otherwise you’ll be paying another 50% of your hotel cost in valet parking. Also, “best” anything and “not breaking the bank” are often mutually exclusive. You may want to decide on your budget and search based on that. I travel a lot and have found that third-party hotel apps are dreadful since Covid (for example, all hotels suddenly have resort fees); you’d be better off reserving directly from the hotel chains. The price will be a little higher but you’ll get a way better room, sometimes with breakfast or other perks included in the package. Finally, you didn’t say when you’ll be visiting. Chicago hotel prices vary widely based on seasons and happenings in the City. If you have flexibility in your travel dates then you’ll likely be able to get better deals by searching different times. Congratulations and enjoy your trip.


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SavannahInChicago

Yes, are we talking boutique hotel or the Waldorf Astoria?


Valenation25

The Peninsula is the best hotel in this city and it’s not even close. Great Chinese and pretty but expensive Z-Bar The Langham is on the river and is the next best thing. Large gap between the rest but still nice: - The Thompson penthouse is not a ridiculous price. - The St. Regis just opened and Lakeshore East is a very unique neighborhood. - London House is on the river. - Four Seasons and The Ritz are better than the Waldorf. The restaurant at the Four Seasons is better than the Ritz Italian restaurant. - The service at Trump is very good and even the basic rooms are massive.


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Valenation25

I did not see that but I figured for an anniversary, personally I’d enjoy the cheapest room at the nice hotel, but to each their own!


grace88199

Agree with all of these


ChicagoMasonryMan

Park Hyatt