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  1. United States
  2. Best Dating Coaches
  3. Dating Coaches in Illinois
  4. Chicago

Best Dating Coaches in Chicago

Chicago Dating Coaches stats: Key insights from this page’s listings Updated
Businesses listed
8
Average rating
3.8 186 reviews
Typical service price
$100 – $225 Median of 20 priced services
Most-offered services
MatchmakingMatchmaking ServicesDating CoachingDate PlanningFeedback Sessions
What customers praise
recommend×33highly recommend×15very professional×8very impressed×7
Dating coachesChicago, IL

1

Its Just Lunch Chicago

Its Just Lunch Chicago specializes in arranging face-to-face first dates, focusing on hand-selected matches and even making restaurant reservations. The team works closely with clients to understand their goals and preferences, helping busy singles enjoy a more personal dating experience. Some find the service less attentive when demand is high, but many appreciate the thoughtful matchmaking and… more...

Its Just Lunch Chicago specializes in arranging face-to-face first dates, focusing on hand-selected matches and even making restaurant reservations. The team works closely with clients to understand their goals and preferences, helping busy singles enjoy a more personal dating experience. Some find the service less attentive when demand is high, but many appreciate the thoughtful matchmaking and organized approach.

Services & Prices
Personalized Matchmaking $300 - $500
Profile Adjustments $100 - $200
Date Setup $50 - $100
Restaurant Reservations $20 - $50
View Profile
(312) 881-5225
Open 9:00 AM - 6:00 PM
121 W Wacker Dr #663, Chicago, IL 60601, USA
General Services
Matchmaking
2

Chicagoland Singles

Chicagoland Singles employs local concierges and dating experts who focus on connecting singles from the Chicago area through personalized introductions and events. They offer professional photo sessions and in-depth interviews to help clients better understand themselves and their dating goals. Some customers appreciate the friendly staff and thoughtful approach, though others have expressed… more...

Chicagoland Singles employs local concierges and dating experts who focus on connecting singles from the Chicago area through personalized introductions and events. They offer professional photo sessions and in-depth interviews to help clients better understand themselves and their dating goals. Some customers appreciate the friendly staff and thoughtful approach, though others have expressed concerns about membership policies and limited matchmaking results.

Services & Prices
Professional Headshots $100 - $300
Portfolio Photo Sessions $200 - $400
Event Photography $150 - $350
Group Dating Events $50 - $100
View Profile
(847) 706-9889
Open 11:00 AM - 7:00 PM
1375 Woodfield Rd #100, Schaumburg, IL 60173, USA
General Services
Photography Services
3

Selective Search

Selective Search applies executive recruitment techniques to matchmaking, focusing on committed individuals across North America. Their thorough interview process evaluates over 100 personal and professional traits to find well-matched partners, with clients appreciating the team’s professionalism and thoughtful communication throughout the search. Some find the process detailed but rewarding.

Services & Prices
Personalized Matchmaking $3000 - $5000
Candidate Profile Creation $0 - $100
View Profile
(312) 396-1200
Open 9:00 AM - 5:00 PM
35 E Wacker Dr #1920, Chicago, IL 60601, USA
General Services
Matchmaking Services
4

Chicago Singles

Chicago Singles specializes in speed dating events designed to connect like-minded professionals across Chicago and nearby suburbs. Their organized gatherings offer a fun, low-commitment way to meet multiple potential matches quickly, though some events have faced criticism for uneven gender ratios. Attendees often appreciate the friendly hosts and the chance to socialize in person.

Services & Prices
Single Men Speed Dating $40 - $60
Single Women Speed Dating $40 - $60
Mixed Group Speed Dating $50 - $70
Themed Singles Parties $30 - $50
View Profile
(888) 729-5552
Open 9:00 AM - 9:00 PM
23 S Dearborn St, Chicago, IL 60603, USA
General Services
Speed Dating Events
5

Stef and the City

With over 14 years of experience, Stef and the City specializes in personalized matchmaking and dating coaching for Chicago singles, including those over 40 and recent college graduates. The team offers honest, direct guidance alongside introductions, and clients appreciate the thoughtful, hands-on support—though some may find the straightforward feedback challenging.

Services & Prices
Personalized Matchmaking $1000 - $3000
Custom Coaching Plan $300 - $600
Online Dating Strategy $150 - $300
Accountability Check-ins $100 - $200
View Profile
(773) 800-2930
Open 9:00 AM - 6:00 PM
3047 N Lincoln Ave #400, Chicago, IL 60657, USA
General Services
Matchmaking
Where they are 8 on the map Click a pin for the profile and directions
6

Ambiance Matchmaking of Chicago

Ambiance Matchmaking specializes in connecting creative leaders and entrepreneurs through personalized, high-quality matchmaking. Founded in 2002, the team arranges thoughtfully planned dates and values client feedback to refine matches. While many appreciate the professional and attentive approach, some find the service pricey and note limited communication with matchmakers.

Services & Prices
Professional Matchmaking $3000 - $5000
Date Coordination $200 - $400
Post-Date Feedback $100 - $200
Group Dating Events $50 - $100
View Profile
(415) 949-1112
Open 9:00 AM - 9:00 PM
220 N Green St, Chicago, IL 60607, USA
General Services
Matchmaking
7

MATCHMAKE CHICAGO

MATCHMAKE CHICAGO works with a diverse clientele, including professionals and creatives, to find meaningful connections through one-on-one matchmaking and detailed consultations. The team offers personalized interviews and a thorough questionnaire to understand client preferences. While some appreciate the genuine approach and ongoing support, others report delays and communication issues after… more...

MATCHMAKE CHICAGO works with a diverse clientele, including professionals and creatives, to find meaningful connections through one-on-one matchmaking and detailed consultations. The team offers personalized interviews and a thorough questionnaire to understand client preferences. While some appreciate the genuine approach and ongoing support, others report delays and communication issues after signing up.

Services & Prices
Personalized Matchmaking $3000 - $4000
Profile Building $150 - $250
Interview Preparation $100 - $200
Singles Mixers $50 - $100
View Profile
Closed Now
1515 22nd St, Oak Brook, IL 60523, USA
General Services
Matchmaking Services
8

Elite Connections Matchmakers Chicago

Elite Connections International, Chicago's top matchmaking agency is a member of the elite group. Our clientele is exclusive and we have 26 years of experience and an A+ rating. Matchmakers in Chicago are committed to helping you find the right person for you. Our ability to meet with clients individually is what we are known for. This allows us to provide a level of service you won't get through… more...

Elite Connections International, Chicago's top matchmaking agency is a member of the elite group. Our clientele is exclusive and we have 26 years of experience and an A+ rating. Matchmakers in Chicago are committed to helping you find the right person for you. Our ability to meet with clients individually is what we are known for. This allows us to provide a level of service you won't get through other online dating sites or dating apps. We have seen the results of our Chicago matchmaking service, as well as personal experience with it. Our Chicago matchmaker will assist you in finding the right person for you. Finding love online is not easy. Our Chicago matchmaking staff will do all the hard work. Elite can help you find your love in Chicago's notoriously difficult dating scene. We are here to assist you in finding the best singles in Chicago. Only serious and sincere people who want to find a meaningful connection. Elite Connections International, Chicago's premier private matchmaking agency is a top choice. Chicago Matchmakers pride themselves on their A+ rating, 28 years of unparalleled achievements, and the thousands of happy clients we have matched.

View Profile
(312) 579-3423
Open 9:00 AM - 6:00 PM
200 W Madison St Ste 2100, Chicago, IL 60606, USA

Latest reviews of Chicago Dating Coaches

Written on TrustAnalytica by clients of the businesses in this list
  • Michael

    My dad signed up with Chicagoland Singles. He paid $9,000.00, met with Chicagoland Singles one time, took a headshot for his profile, and never went out on a single date. When I found out that my dad signed up with Chicagoland Singles, I immediately e-mailed Chicagoland Singles and told them that my…

Chicago Dating Coaches stats: 8 businesses compared side by side · updated
# Business Rating Reviews Starting price Phone Website
1 Its Just Lunch Chicago 4.3 99 $20 (312) 881-5225 Visit
2 Chicagoland Singles 3.5 32 $20 (847) 706-9889 Visit
3 Selective Search 4.2 16 $100 (312) 396-1200 Visit
4 Chicago Singles 4.6 11 $25 (888) 729-5552 Visit
5 Stef and the City 4.0 8 $50 (773) 800-2930 Visit
6 Ambiance Matchmaking of Chicago 4.0 7 $50 (415) 949-1112 Visit
7 MATCHMAKE CHICAGO 2.5 11 $50 — Visit
8 Elite Connections Matchmakers Chicago 3.0 2 — (312) 579-3423 Visit

Frequently asked questions

7 questions
How much do dating coaches in Chicago typically charge?
Dating coach fees in Chicago vary widely based on services offered. Commonly, fees are structured per session or as a package. Free consultations are sometimes available.
How do I choose the best dating coach in Chicago?
Consider customer reviews, ratings, and if the business has claimed its profile. TrustAnalytica ranks based on these factors for transparency and data-driven results.
What questions should I ask a dating coach before hiring?
Inquire about their experience, success stories, methods, and fees. Ask if they offer free consultations to ensure their services align with your needs.
Do dating coaches in Chicago offer free consultations?
Free consultations are sometimes offered by dating coaches in Chicago, allowing you to assess their approach and compatibility with your goals.
What services do dating coaches provide?
Dating coaches offer personalized advice on dating strategies, confidence building, communication skills, and relationship management, tailored to individual needs.
Do I need a dating coach?
Consider a dating coach if you seek personalized guidance to improve dating skills, overcome challenges, or achieve specific relationship goals.
How long does the dating coaching process take?
The duration varies based on individual goals and progress. Some clients engage for a few sessions, while others may continue longer for ongoing support.

Our Methodology

Best 10 dating coaches list assembly and recognition by TrustAnalytica for Chicago is based on online reputation backed by review sources as google reviews, TrustAnalytica reviews and more.

We choose the best companies in the location and rank them based on rating, quantity of reviews and verification (Claimed or unclaimed profile).

Rankings are frequently updated to reflect the latest reviews from trusted sources.

Profile verification is free and may improve ranking, as we prioritize accurate, up-to-date profiles that are actively maintained and regularly reviewed.

TrustAnalytica's procedure for listing dating coaches companies involves manual research, review and placement. Please note that some companies are placed here through their registration with our services as every company gets not only access to our Saas services but also a profile that gets listed. We evaluate businesses based on their online reputation, accessibility, online resources such as website and their fit for best 10 dating coaches category.

The Process

1

Business Verification

Verified dating coaches listings in Chicago are based on robust online activity and Google reviews, ensuring credibility.

2

Business Details

Comprehensive dating coaches profiles offer vital details for informed decisions in Chicago.

3

Reviews And Ratings

Real-time customer ratings guide our dating coaches rankings in Chicago, reflecting genuine reputation.

4

SEO And Keywords

Our SEO strategy elevates the visibility of top dating coaches providers in Chicago.

5

AI Search Visibility

Every dating coaches listing in Chicago is published with structured data that AI search tools like ChatGPT, Perplexity and Google AI Overviews can read and cite.