The Windy City is a summertime destination that is hard to resist. From June to August, it is simply hard to beat walking around downtown Chicago or cruising around the lake with the sun shining.
Chicago is known for its beautiful downtown architecture, museums, green spaces in Millennium Park, pro sports with the Bears, Blackhawks, Bulls, and Cubs, upscale shopping along the Magnificent Mile, award-winning restaurants, and the comedy scene at Second City.
As we covered in our guides to the best hotels in New York City and Washington, D.C., Chicago has a ton of points hotel possibilities. We will touch on all of your options, but most importantly we will show you how to receive the most value.
42 Chicago hotels were evaluated across the 4 major hotel brands of Hilton, Hyatt, IHG, and Marriott for this article. The hotels were ranked using a cents per point value with the goal to show you the types of value you can receive.
With this analysis, we’re using our hotel cents per point value as the benchmark to show you the value you can receive, but it’s also important to consider what value we assign to each program’s points.
Best Value Chicago Hotels
With our goals and methodology for this hotel evaluation in mind, let’s highlight the best hotels that you can book with points in Chicago.
When Hyatt acquired Joie de Vivre (now JdV by Hyatt), the brand picked up several boutique properties in cities throughout the U.S., including Baltimore, New York City, and San Francisco. The Lincoln is one of these properties and dates back to the 1920s. Amenities available to guests include a gym, a farm-to-table restaurant, a rooftop lounge, bike rentals, pedicabs, rooftop yoga classes, and a wine hour.
During peak travel dates, this hotel averages more than $400 per night. However, Hotel Lincoln only requires 12,000 points per night. This results in a cents per point value of 3.5.
Hot Tip: A guest amenity fee of $15 will apply to each night of your stay. The amenity fee includes 1 drink per stay, seasonal bike rentals, and pedicab tours, and discounted daily passes to the Equinox gym.
Hyatt Points Required: 12,000
June-August Rate: $415
Points Value: 3.5 cents per point
Located a short walk from Millennium Park is where you will find Hyatt Place Chicago/Downtown-The Loop. Inside this category 4 hotel, you will find a bar/cafe, an indoor pool, and a gym.
The Hyatt Place Chicago/Downtown-The Loop requires 15,000 points or averages $402 per night. Guests can expect to receive 2.7 cents per point during peak travel dates.
Hyatt Points Required: 15,000
June-August Rate: $402
Points Value: 2.7 cents per point
The Unbound Collection, of which the Chicago Athletic Association is a property, has a solid line up of U.S. hotels including properties in Austin, Carmel, Miami, Nashville, New Orleans, and Philadelphia.
This Chicago Athletic Association was once an exclusive sportsmen’s club and now features a rooftop restaurant, a speakeasy-style bar, a game room, and a gym.
What makes this Category 4 Hyatt even better is that you will likely receive 2.6 cents per point in value during peak travel dates. That’s 15,000 points per night when the cash rates are nearly $400 per night.
Hot Tip: The Chicago Athletic Association charges guests a $25 nightly Founder’s Fee. This fee includes a welcome champagne toast in the Cherry Circle Room, expedited entry to the rooftop restaurant, seasonal bike rentals, and access to the only Shake Shack in-room dining service in the world.
Hyatt Points Required: 15,000
June-August Rate: $388
Points Value: 2.6 cents per point
Just a short walk from Wrigley Field baseball park, Hotel Zachary is a boutique hotel in the Lakeview neighborhood. Amenities available to hotel guests include a gym and a bar with an all-day menu.
Hotel Zachary averages nearly $529 per night during peak travel dates. Hotel guests can expect to receive right at 1.5 cents per night when 35,000 points per night are a minimum of what you will need to book an award stay.
Marriott Points Required: From 35,000
June-August Rate: $529
Points Value: 1.5 cents per point
The Robey is a Design Hotels property located in a 1920s building offering guests a boutique hotel experience. Amenities include an American/French restaurant, a lounge, a rooftop terrace with a bar, and an outdoor pool.
You can book this hotel starting at 35,000 points per night or pay just under $429 per night. This means that your Marriott points will be worth 1.2 cents per point.
Marriott Points Required: From 35,000
June-August Rate: $429
Points Value: 1.2 cents per point
Travelers looking to stay in a Luxury Collection Hotel should check out The Gwen. As a hotel guest, you’ll have access to an American restaurant, a terrace bar, a gym, and a lounge.
1.2 cents per point is the value that you can expect to receive as a guest during peak travel dates. Cash rates hover around $423 per night during this time while a minimum of 35,000 points per night are what you will need to book an award stay.
Marriott Points Required: From 35,000
June-August Rate: $351
Points Value: 2.3 cents per point
Located inside a converted early 1900s hat factory, Kimpton Hotel Monaco is an IHG hotel that provides a boutique experience. Guests have access to evening wine, loaner bikes, a restaurant, and a gym.
Starting at 37,500 points per night, the Kimpton Hotel Monaco cash rates are not cheap as they average $434 per night. This means that your IHG points will be worth 0.9 cents per point during peak travel dates.
IHG Points Required: 37,500-50,000
June-August Rate: $434
Points Value: 0.9-1.1 cents per point
InterContinental Chicago Magnificent Mile (IHG Rewards)
The InterContinental Chicago Magnificent Mile is an iconic IHG property that dates all the way back to 1929.
Located just a short walk from Millennium Park and the lakefront Chicago Shakespeare Theater, this property has a fine-dining steakhouse by basketball legend Michael Jordan, a wine bar, a Starbucks coffee shop, and a breakfast restaurant, as well as an indoor pool, a spa, and a gym.
IHG Points Required: 35,000-50,000
June-August Rate: $300-$525
Points Value: 0.8-1.1 cents per point
Travelers wanting to book a stay near downtown Chicago should consider the Waldorf Astoria Chicago. Amenities available to guests include a European bistro, a cocktail bar, a spa, a gym, and a lap pool.
95,000 points per night are the number of points you will need to book an award night at this property. Peak travel dates require $608 per night resulting in a cents per point value of 0.6.
Hilton Points Required: 95,000
June-August Rate: $608
Points Value: 0.6 cents per point
Flanking Grant Park is the Hilton Chicago. If you stay at this hotel, you’ll have access to an Irish pub, a bar and grill restaurant, a coffee shop, a gym, and an indoor pool.
The Hilton Chicago can be booked for $317 per night or with 50,000 points per night. This means that guests can expect to receive 0.6 cents per point in value.
Hilton Points Required: 50,000-60,000
June-August Rate: $317
Points Value: 0.6 cents per point
Earn Hotel Points to Redeem in Chicago
After reading through our hotel list, the first thing that likely comes to mind is how to earn the points that you’ll need. The great news is that we have you covered to make any of these redemptions a reality. Let’s start with World of Hyatt and work our way through each of the hotel loyalty programs.
World of Hyatt
The World of Hyatt Credit Card
For any traveler, and especially the true road warriors, the $95 annual fee World of Hyatt card is a card to snag sooner rather than later.
Hyatt made several changes to this credit card in 2019 that it will implement in 2020, most of which are rewarding for current and potential cardmembers. The team at Hyatt had customers in mind with the card relaunch as the benefits and perks make this credit card one to keep year after year.
We are huge fans of the Hyatt Credit Card, but is this card one every traveler should apply for? What if you are not a road warrior or loyal to Hyatt? Does it make sense to be a cardmember? In our opinion, the answer is a resounding yes!
The Hyatt Credit Card offers a ton of upside, including the following benefits and perks:
- Up to 9x points at Hyatt — 4x points per $1 at Hyatt plus 5x base points per $1 as a Hyatt member
- 1 free night at a Category 1-4 property after your cardmember anniversary
- 1 additional free night at a Category 1-4 property after spending $15,000 during your cardmember year
- 5 elite night qualifying credits
- 2 additional elite night credits for every $5,000 spent on the card
- Complimentary World of Hyatt Discoverist status for as long as your account is open
Unlike other hotel credit cards, the Hyatt Credit Card is one that makes sense to spend on throughout the year. The reason is that Hyatt awards cardmembers with 2 elite nights with every $5,000 spent on the card. For those of you wanting to earn top tier Globalist status, this elite night perk through spending goes a long way towards earning that status.
The last benefit we will cover is geared towards heavy spenders. For readers who can spend $15,000 on the card in a cardmember year, you will earn 1 additional Category 1-4 free night certificate. This certificate is in addition to the anniversary certificate that comes with the card. By spending $15,000 in a cardmember year, you will earn 2 Category 1-4 free night certificates, enough for a weekend trip!
Hot Tip: If you’re a small business owner, consider signing up for the World of Hyatt Business Credit Card, which offers big earning potential and an easier path to Globalist status.
World of Hyatt Award Chart
|World of Hyatt Award Chart|
|Hotel Category||Off-Peak Points Per Night||Standard Points Per Night||Peak|
Points Per Night
Other Ways to Earn World of Hyatt Points
The most efficient way to earn Hyatt points is with the Hyatt Credit Card. As mentioned earlier, cardmembers will earn 9x points at Hyatt — 5x points as a Hyatt member plus 4x points with the Hyatt Credit Card.
One of the most valuable Chase Ultimate Rewards travel partners in the World of Hyatt program. When you earn Chase Ultimate Rewards points, these points can be transferred directly to Hyatt. Chase has no shortage of credit cards that earn Chase points, so you will be able to easily earn the Hyatt points that you need via Chase for Hyatt point transfers.
The Chase Sapphire Preferred® Card, Chase Sapphire Reserve®, and Ink Business Preferred® Credit Card are the 3 Chase credit cards that earn Chase points directly with your spend.
In addition to the Chase Ultimate Rewards credit cards, Chase also allows you to convert cash-back earned into Chase points if you also hold a Chase Ultimate Rewards card. The cash-back credit cards that we recommend are the Chase Freedom® card (no longer open to new applicants), Chase Freedom Flex℠, Chase Freedom Unlimited®, Ink Business Cash® Credit Card, and Ink Business Unlimited® Credit Card.
Marriott Bonvoy Credit Cards
There are 4 co-branded credit cards offered by Marriott. Each is focused on a different type of traveler, which is great news! Let’s outline the cards that are at your disposal.
Marriott Bonvoy Award Chart
Marriott uses dynamic pricing for its hotels, which means the number of points you’ll pay will vary based on demand.
Other Ways to Earn Marriott Points
The easiest way to earn Marriott points is to put your spending on its credit cards. You can also pay for cash stays at Marriott where you’ll earn 10 points per $1 spent as a Marriott member and 10-75% bonus points depending upon your Marriott elite member tier.
American Express and Chase points transfer to Marriott, however, we recommend that you transfer American Express and Chase points to their high-value airline (and hotel with Hyatt and Chase) partners instead.
IHG Rewards Credit Cards
Chase is the sole issuer of IHG credit cards. These cards are co-branded by Chase and are subject to the Chase 5/24 rule. Before applying for any of the IHG cards, it’s important to check your 5/24 status.
The IHG® Rewards Premier Credit Card used to be the IHG® Rewards Club Select credit card (no longer open to new applicants).
There are 3 reasons to apply for the IHG Premier card:
- Cardmembers receive IHG elite status
- The annual certificate for a property requiring up to 40,000 points per night
- Reward night free on an eligible award booking
The other personal card issued by Chase is the IHG® Rewards Traveler Credit Card. The ability to earn additional points at IHG properties and the ability to receive an award night when you redeem points for any stay of 4 or more nights are 2 reasons to apply for this card.
IHG Rewards Award Pricing
Similar to Hilton, IHG’s award pricing structure is now 100% dynamic. The price of reward nights will fluctuate depending on factors like the cash price of the hotel, the seasonality of the location, etc.
Other Ways to Earn IHG Rewards Points
You can earn IHG points by spending on IHG credit cards and staying at IHG hotels. Chase points transfer directly to IHG, however, we do not recommend that you make this transfer. Instead, redeem Chase points with its more valuable airline and hotel partners.
Hilton Honors Credit Cards
The Hilton Honors program partners with American Express to issue several credit cards geared towards all types of travelers.
Offering free weekend night certificates for a standard room is the strategy Hilton uses to incentivize new credit card signups. Cards that come with certificates do have annual fees, however, the certificate easily offset the fees.
The Hilton Aspire card is the premium card of the bunch that offers cardmembers a free weekend night certificate. An earn an additional free weekend night certificate can be earned if you’re a Hilton Surpass cardmember. If you want to earn a second weekend night certificate, simply spend $15,000 in a calendar year on this card.
The Hilton Business Amex card is great for business owners. You can earn a free weekend night certificate by spending $15,000 in a cardmember year on this card. If you spend $45,000 in a cardmember year, you will earn an additional free weekend night certificate.
Hilton Honors Award Chart
You will not find an award chart with the Hilton Honors program. Hilton uses dynamic award pricing so the number of points required per night will change.
We have found the Points Explorer tool to help determine the number of points per night you’ll need. Enter your destination in the Where do you want to go? search bar. Then enter the number of points that you have in the How many Points per night are you working with? scroll bar. Last, the search results will show you how many points you will need to book a hotel in that area.
Other Ways to Earn Hilton Honors Points
Hilton credit card spending is the most efficient way to earn Hilton points. Another way to earn Hilton points is to pay for cash stays at Hilton properties and take Lyft rides. Point transfers from American Express are possible, however, we do not recommend transferring Amex points to Hilton.
Using points to book a hotel award stay in Chicago provides you with 2 things: a ton of value with your hard-earned hotel points and the ability to reduce your cash spend during your time in the city.
As you’ve likely seen, it’s hard to go wrong with using points to book any of the hotels on this list. Based on our analysis, the cents per point value will range from 0.4-3.6. Whatever hotel you decide to book, we’re confident that you can redeem hotel points for value for your next trip to the Windy City.
The information regarding The Hilton Honors American Express Surpass® Card and Hilton Honors American Express Aspire Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.
For rates and fees of the Marriott Bonvoy Business® American Express® Card, click here.
For rates and fees of the Marriott Bonvoy Brilliant™ American Express® Card, click here.
For rates and fees of the Hilton Honors American Express Card, click here.
For rates and fees of The Hilton Honors American Express Business Card, click here.