The 10 Best Chicago Hotels to Book With Points [for Max Value]

Chicago Buckingham Fountain

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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.

Hotel Lincoln

Hotel Lincoln Hyatt
Spend time at Hotel Lincoln, a boutique hotel in Chicago. Image Credit: Hyatt

When Hyatt acquired Joie de Vivre, 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. 

Category: 3

Hyatt Points Required: 12,000

June-August Rate: $415

Points Value: 3.5 cents per point

Hyatt Place Chicago/Downtown-The Loop

Hyatt Place Chicago Downtown The Loop Exterior
Who said a Hyatt Place property can’t provide a ton of value? Hyatt Place Chicago/Downtown-The Loop. Image Credit: Hyatt

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.

Category: 4

Hyatt Points Required: 15,000

June-August Rate: $402

Points Value: 2.7 cents per point

Chicago Athletic Association

Chicago Athletic Association Bar
Find old school luxury at the Chicago Athletic Association. Image Credit: Hyatt

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. 

Category: 4

Hyatt Points Required: 15,000

June-August Rate: $388

Points Value: 2.6 cents per point

Hotel Zachary, Chicago, a Tribute Portfolio Hotel

Hotel Zachary Chicago a Tribute Portfolio Hotel Bar View
Redeem Marriott points for value at Hotel Zachary. Image Credit: Marriott

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 is a category 5 hotel that averages nearly $529 per night during peak travel dates. Hotel guests can expect to receive right at 1.5 cents per night as 35,000 points per night are what you will need to book an award stay.

Category: 5

Marriott Points Required: 35,000

June-August Rate: $529

Points Value: 1.5 cents per point

The Robey, Chicago, a Member of Design Hotels™

The Robey Chicago a Member of Design Hotels Outdoor Pool View
Experience a boutique hotel stay at The Robey Chicago. Image Credit: Marriott

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 for 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.

Category: 5

Marriott Points Required: 35,000

June-August Rate: $429

Points Value: 1.2 cents per point

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen a Luxury Collection Hotel Michigan Avenue Chicago Exterior View
The Gwen is a Luxury Collection Hotel that can be booked with Marriott points. Image Credit: Marriott

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 35,000 points per night are what you will need to book an award stay.

Category: 4

Marriott Points Required: 15,000

June-August Rate: $351

Points Value: 2.3 cents per point

Kimpton Hotel Allegro

Kimpton Hotel Allegro Exterior View
Redeem IHG points for a boutique hotel stay at Kimpton Hotel Allegro. Image Credit: IHG

Within the Loop is where you’ll find the Kimpton Hotel Allegro. If you stay at this hotel, amenities include nightly wine receptions, an Italian restaurant, a cocktail bar, and a gym.

Kimpton Hotel Allegro averages nearly $367 per night during peak travel dates. You can book this hotel with 40,000 points per night resulting in a 0.9 cents per point value.

Category: 7

IHG Points Required: 40,000

June-August Rate: $367

Points Value: 0.9 cents per point

Kimpton Hotel Monaco Chicago

Kimpton Hotel Monaco Chicago Bedroom View
Kimpton Hotel Monaco is another IHG Chicago property that you can book with points. Image Credit: IHG

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.

At 50,000 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.

Category: 9

IHG Points Required: 50,000

June-August Rate: $434

Points Value: 0.9 cents per point

Waldorf Astoria Chicago

Waldorf Astoria Chicago Exterior View
Find value with your Hilton points at the Waldorf Astoria Chicago. Image Credit: Hilton

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

Hilton Chicago

Hilton Chicago Exterior View
Redeem points for a stay at the Hilton Chicago. Image Credit: Hilton

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

World of Hyatt Credit Card

For any traveler, and especially the true road warriors, the $95 annual fee Hyatt Credit 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!

World of Hyatt Credit Card - Earn 25,000 Bonus Points after $3,000 in purchases within 3 months of account opening. Plus, earn an additional 25,000 Bonus Points after $6,000 total in purchases within 6 months of account opening.

We like how you also get one free night at any Category 1–4 Hyatt hotel (or resort) every year after your cardmember anniversary. See how to best use your free night for maximum value!

The Hyatt Credit Card offers a ton of upside, including the following benefits and perks:

  • 50,000-60,000 point signup bonus
  • 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
  • Discoverist status as long as you have the card

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!

World of Hyatt Award Chart

World of Hyatt has announced unfortunate changes to its award chart, which are now delayed to start in 2021. Whenever we in the points and miles world hear that award chart changes are coming to an airline or hotel program, it usually means for the worse.

While it is true that Hyatt hotels will have peak pricing in the future, travelers will also have the option to book off-peak pricing. This means that you’ll be able to save anywhere between 1,500-5,000 points per night during off-peak dates. The current award chart is below.

World of Hyatt Award Chart
Hotel CategoryStandard Room Points per NightRegency/Grand Club Points per NightStandard Suite
Points per Night
Premium Suite Points per Night
15,0007,0008,00010,000
28,00012,00013,00016,000
312,00017,00020,00024,000
415,00021,00024,00030,000
520,00027,00032,00040,000
625,00033,00040,00050,000
730,00039,00048,00060,000
840,000

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® card, 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, Chase Freedom Unlimited® card, Ink Business Cash℠ Credit Card, and Ink Business Unlimited℠ Credit Card.

Marriott Bonvoy

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 Boundless™ Credit Card - Earn 5 Free Nights after spending $5,000 on purchases in the first 3 months from account opening. Get automatic silver elite status each account anniversary year; and a free night award (valued up to 35,000 points) every year after account anniversary. Plus, earn 6X points per $1 at over 7,000 participating Marriott Bonvoy hotels, and 2X points per $1 on all other purchases. Annual Fee is $95.
Marriott Bonvoy Bold™ Credit Card - Earn 30,000 bonus points when you spend $1,000 on purchases in the first 3 months of account opening. Earn 3X points per $1 at participating Marriott Bonvoy hotels, earn 2X on other travel purchases, then 1x on all other purchases. A solid card for Marriott loyalists looking for a no-annual-fee card offering Marriott Bonvoy Silver Elite status.
Marriott Bonvoy Business™ American Express® Card - earn 100,000 bonus points when you spend $5,000 on purchases in the first 3 months of account opening. A solid card for business owners who will get complimentary Marriott Bonvoy silver elite status. Annual fee is $125. Terms Apply. For rates and fees of the Marriott Bonvoy Business Card, click here.
Marriott Bonvoy Brilliant™ American Express® Card - Earn 125,000 bonus points! Earn 100,000 bonus points after you spend $5,000 in purchases on your new Card in your first 3 months. Plus, earn an additional 25,000 bonus points after your first anniversary of Card Membership. Offer Expires 1/13/2021.

Earn 6x per $1 at participating Marriott Bonvoy hotels plus 3x at U.S. restaurants and flights booked directly with airlines. Annual fee is $450. Terms Apply. For rates and fees of the Bonvoy Brilliant card, click here.

Marriott Bonvoy Award Chart

Marriott utilizes off-peak, standard, and peak pricing. As you can see, there’s an opportunity to save between 5,000-30,000 points per night if you book off-peak award dates.

Marriott Bonvoy Award Chart
Hotel CategoryOff-Peak Points per NightStandard Points per NightPeak Points per Night
15,0007,50010,000
210,00012,50015,000
315,00017,50020,000
420,00025,00030,000
530,00035,00040,000
640,00050,00060,000
750,00060,00070,000
870,00085,000100,000

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 Club

IHG Rewards Club 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.

CREDIT CARDCARD INFO
IHG® Rewards Club Traveler Credit Card

IHG® Rewards Club Traveler Credit Card
  • Earn 100,000 bonus points after spending $2,000 on purchases in the first 3 months from account opening
  • Earn up to 15 points total per $1 spent when you stay at an IHG hotel
  • Earn 2x points on purchases at gas stations, grocery stores, and restaurants; then 1 point per $1 on all other purchases.
  • No Annual Fee
IHG® Rewards Club Premier Credit Card

IHG® Rewards Club Premier Credit Card
  • Earn 140,000 bonus points after spending $3,000 on purchases in the first 3 months from account opening
  • Earn up to 25 points total per $1 spent when you stay at an IHG hotel
  • Earn 2x points on purchases at gas stations, grocery stores, and restaurants; then 1 point per $1 on all other purchases.
  • Annual Fee: $0 for the first year, $89 thereafter

IHG® Rewards Club Premier Credit Card

The IHG Premier 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:

  1. Cardmembers receive IHG elite status
  2. The annual certificate for a property requiring up to 40,000 points per night
  3. Fourth night free on an award booking

IHG® Rewards Club Traveler Credit Card

The other card issued by Chase is the IHG Traveler 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 Club Award Chart

There is no IHG award chart available, so we’ve created one below for your reference. IHG has 13 hotel categories that range from 10,000-70,000 points per night.

IHG utilizes fixed award pricing similar to Hyatt and Marriott, and unlike what you’ll see with Hilton.

IHG Rewards Club Award Chart
CategoryPoints per Night
110,000
215,000
320,000
425,000
530,000
635,000
740,000
845,000
950,000
1055,000
1160,000
1265,000
1370,000

Other Ways to Earn IHG Rewards Club 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

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. 

Final Thoughts

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.


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 Aspire Card, click here.
For rates and fees of the Hilton Honors American Express Surpass® 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.


Frequently asked questions

What's the best hotel to stay at in Chicago?

As we have shown in this article, Chicago has a multitude of hotels that you can book with hotel points. We recommend checking out Hotel Lincoln, Chicago Athletic Association, Hotel Zachary, The Robey, The Gwen, Kimpton Allegro, Kimpton Hotel Monaco, and the Waldorf Astoria in Chicago.

Where should I stay in Chicago for attractions?

Gold Coast, Magnificent Mile, and River North provide easy access to the attractions and sites that Chicago has to offer. Each of these neighborhoods has hotels that you can book with your hotel points.

What food is Chicago famous for?

Deep-dish pizza is one of the city’s most famous foods that any new and repeat visitor should try. Chicago is also known for its hot dogs, Italian, and steak restaurants. There is no shortage of establishments that you can find your fix at with any of these foods.

What is the Magnificent Mile Chicago?

The Magnificent Mile is an upscale district in downtown Chicago with retail, restaurants, museums, and hotels along Michigan Avenue. This district runs from the Chicago River to Oak Street in the Near North Side.

What is considered the Loop in Chicago?

The Loop is the central business district of Chicago and the main part of its downtown scene. This area is the second-largest commercial business district in North America after Midtown Manhattan in New York City.

Michael McHugh

About Michael McHugh

Born and raised in Mobile, Alabama, Michael took his first international trip in 2013 with friends to the Bahamas. Although he didn't travel much in his younger years, on that trip, he caught the travel bug and has been hooked ever since. Michael first caught wind of the points and miles game in 2014 while at a bar in Washington, DC where the conversation amongst friends was quickly derailed because of an alert on a friend's phone about a mistake fare.  That's where the love affair with points and miles began.

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